Polar group-containing olefin copolymer

ABSTRACT

To provide a novel polar group-containing olefin copolymer in which an enone structure is introduced into the main chain as a structural unit. A polar group-containing olefin copolymer comprising a structural unit (A) derived from one or more monomers selected from the group consisting of ethylene and an olefin containing 3 to 20 carbon atoms, and a structural unit (B) represented by the following general formula (I):(Rx and Ry in the general formula (I) are as described in the Description.)

TECHNICAL FIELD

The disclosure relates to a novel polar group-containing olefincopolymer. In particular, the disclosure relates to a novel polargroup-containing olefin copolymer in which an enone structure isintroduced into the main chain.

BACKGROUND ART

Recently, there is an increasing need for a polar group-containingolefin copolymer in which a polar group is introduced into polyolefin,and there are reports of various copolymer examples.

As the polar group-containing olefin copolymer, a copolymer in which apolar group is contained in a side chain is conventionally known. Forexample, there is a copolymer as shown in FIG. 16, which is obtained bycopolymerization of ethylene and an acrylic acid ester or a vinyl ketoneand in which a carbonyl group is contained in a side chain (for example,Patent Literature 1).

As the polar group-containing olefin copolymer in which a polar group isintroduced into the main chain of polyolefin, there is a copolymer asshown in FIG. 17, which is obtained by copolymerization of α-olefin andcarbon monoxide and in which a carbonyl group is contained in the mainchain (for example, Patent Literatures 2 and 3).

CITATION LIST Patent Literatures

-   Patent Literature 1: Japanese Patent No. 6309206-   Patent Literature 2: U.S. Pat. No. 3,694,412-   Patent Literature 3: U.S. Pat. No. 3,689,460

SUMMARY OF INVENTION Technical Problem

However, the copolymer as described in Patent Literature 1, which is aconventional copolymer of a polar group-containing monomer and α-olefin,is a polymer that contains a functional group only in a side chain.Conventional copolymerization of a polar group-containing monomer andα-olefin cannot introduce a functional group into the main chain of thepolymer chain.

Copolymerization of α-olefin and carbon monoxide as described in PatentLiteratures 2 and 3 can introduce a carbonyl group into the main chainof the polymer chain. However, a functional group different from acarbonyl group cannot be introduced into the main chain of a polymer.The copolymerization of α-olefin and carbon monoxide cannot introduce anenone structure, which is an unsaturated bond structure forming theconjugated system of alkene and ketone, as a structural unit of thepolymer chain.

An object of the present application is to provide a novel polargroup-containing olefin copolymer in which, as a structural unit, anenone structure is introduced into the main chain of the polymer chain.

Solution to Problem

The polar group-containing olefin copolymer of the present disclosure isa polar group-containing olefin copolymer comprising a structural unit(A) derived from one or more monomers selected from the group consistingof ethylene and an olefin containing 3 to 20 carbon atoms, and astructural unit (B) represented by the following general formula (I):

where R^(x) and R^(y) are each independently a hydrogen atom, a halogenatom, a hydroxyl group, a formyl group, an ester group containing 1 to30 carbon atoms, an acyloxy group containing 1 to 30 carbon atoms, anacyl group containing 1 to 30 carbon atoms, an alkoxy group containing 1to 30 carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, analkylthio group containing 1 to 30 carbon atoms, an arylthio groupcontaining 6 to 30 carbon atoms, a nitro group, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or R^(x) and R^(y) are optionally bound to each other toform a 4- to 10-membered ring.

In the polar group-containing olefin copolymer of the presentdisclosure, from the viewpoint of copolymer production efficiency, thestructural unit (B) represented by the general formula (I) is preferablyderived from one or more monomers selected from the group consisting ofpolar group-containing monomers represented by the following generalformula (1):

where R^(x) and R^(y) are each independently a hydrogen atom, a halogenatom, a hydroxyl group, a formyl group, an ester group containing 1 to30 carbon atoms, an acyloxy group containing 1 to 30 carbon atoms, anacyl group containing 1 to 30 carbon atoms, an alkoxy group containing 1to 30 carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, analkylthio group containing 1 to 30 carbon atoms, an arylthio groupcontaining 6 to 30 carbon atoms, a nitro group, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or R^(x) and R^(y) are optionally bound to each other toform a 4- to 10-membered ring.

In the polar group-containing olefin copolymer of the presentdisclosure, at least one of R^(x) and R^(y) is preferably different froma hydrogen atom, from the viewpoint of a wider range of applications ofthe polar group-containing olefin copolymer and from the viewpoint ofthe stability of the compound represented by the general formula (1).

The polar group-containing olefin copolymer of the present disclosuremay further comprise a structural unit (C) derived from one or moremonomers selected from the group consisting of a polar group-containingmonomer (c-1) represented by the following general formula (2) and apolar group-containing monomer (c-2) represented by the followinggeneral formula (3):

where R¹ and R² are each independently a hydrogen atom, an ester groupcontaining 1 to 30 carbon atoms, an acyloxy group containing 1 to 30carbon atoms, an alkoxy group containing 1 to 30 carbon atoms, anaryloxy group containing 6 to 30 carbon atoms, a cyano group, an aminogroup optionally being substituted with a hydrocarbon group containing 1to 30 carbon atoms, an amide group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an imino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, or a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atom,a nitrogen atom and a phosphorus atom, and at least one of R¹ and R² isa group containing at least one of an oxygen atom and a nitrogen atom,and

where R³ to R¹⁰ are each independently a hydrogen atom, a halogen atomor a hydrocarbon group containing 1 to 20 carbon atoms; n is 0 or apositive integer, and when n is 2 or more, R⁷ to R¹⁰ are each optionallythe same or different in each repeating unit; R¹¹ to R¹⁴ are eachindependently a hydrogen atom, an ester group containing 1 to 30 carbonatoms, an acyloxy group containing 1 to 30 carbon atoms, an alkoxy groupcontaining 1 to 30 carbon atoms, an aryloxy group containing 6 to 30carbon atoms, a cyano group, an amino group optionally being substitutedwith a hydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, an imino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, or a hydrocarbongroup containing 1 to 30 carbon atoms and optionally being substitutedwith a functional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom, a nitrogen atom and aphosphorus atom, and at least one of R¹¹ to R¹⁴ is a group containing atleast one of an oxygen atom and a nitrogen atom; and R¹¹ and R¹² areoptionally integrated to form a divalent organic group, and R¹³ and R¹⁴are optionally integrated to form a divalent organic group; R¹¹ or R¹²optionally forms a ring with R¹³ or R¹⁴.

In the polar group-containing olefin copolymer of the presentdisclosure, from the viewpoint of polymer production efficiency, thestructural unit (A) is preferably a structural unit derived fromethylene.

In the polar group-containing olefin copolymer of the presentdisclosure, from the viewpoint of enhancing the applicability of thepolar group-containing olefin copolymer and from the viewpoint of thestability of the compound represented by the general formula (1), it ispreferable that R^(x) and R^(y) are each independently a hydrogen atom,a hydroxyl group, a formyl group, an ester group containing 1 to 30carbon atoms, an acyl group containing 1 to 30 carbon atoms, an alkoxygroup containing 1 to 30 carbon atoms, an amino group optionally beingsubstituted with a hydrocarbon group containing 1 to 30 carbon atoms, asilyl group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, a halogen-substituted hydrocarbon groupcontaining 1 to 30 carbon atoms, a hydrocarbon group containing 1 to 30carbon atoms and optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom, or a heterocyclic groupoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or R^(x) and R^(y) are optionally bound to eachother to form a 4- to 10-membered ring, and at least one of R^(x) andR^(y) is different from a hydrogen atom.

In the polar group-containing olefin copolymer of the presentdisclosure, from the viewpoint of enhancing the applicability of thepolar group-containing olefin copolymer, it is preferable that R^(x) andR^(y) are each independently a halogen atom, a hydroxyl group, a formylgroup, an ester group containing 1 to 30 carbon atoms, an acyloxy groupcontaining 1 to 30 carbon atoms, an acyl group containing 1 to 30 carbonatoms, an alkoxy group containing 1 to 30 carbon atoms, an aryloxy groupcontaining 6 to 30 carbon atoms, an alkylthio group containing 1 to 30carbon atoms, an arylthio group containing 6 to 30 carbon atoms, anamino group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, a silyl group optionally beingsubstituted with a hydrocarbon group containing 1 to 30 carbon atoms, anamide group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, a halogen-substituted hydrocarbon groupcontaining 1 to 30 carbon atoms, a hydrocarbon group containing 1 to 30carbon atoms and optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom, or a heterocyclic groupoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or R^(x) and R^(y) are optionally bound to eachother to form a 4- to 10-membered ring.

In the polar group-containing olefin copolymer of the presentdisclosure, from the viewpoint of enhancing the applicability of thepolar group-containing olefin copolymer, it is preferable that R^(x) andR^(y) are each independently a hydroxyl group, a formyl group, an estergroup containing 1 to 30 carbon atoms, an acyl group containing 1 to 30carbon atoms, an alkoxy group containing 1 to 30 carbon atoms, an aminogroup optionally being substituted with a hydrocarbon group containing 1to 30 carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, a halogen-substitutedhydrocarbon group containing 1 to 30 carbon atoms, a hydrocarbon groupcontaining 1 to 30 carbon atoms and optionally being substituted with afunctional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom and a nitrogen atom, or aheterocyclic group optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom, or R^(x) and R^(y) areoptionally bound to each other to form a 4- to 10-membered ring.

Advantageous Effects of Invention

According to the present disclosure, a novel polar group-containingolefin copolymer in which, as a structural unit, an enone structure isintroduced into the main chain of the polymer chain, can be provided.

BRIEF DESCRIPTION OF DRAWINGS

In the accompanying drawings,

FIG. 1 shows the ¹H-NMR measurement results of the polargroup-containing olefin copolymers 1 to 4 of Examples 1 to 4;

FIG. 2 shows the ¹H-NMR measurement result of the polar group-containingolefin copolymer 1 of Example 1;

FIG. 3 shows the ¹³C-NMR measurement result of the polargroup-containing olefin copolymer 1 of Example 1;

FIG. 4 shows the GPC chart of the polar group-containing olefincopolymer 1 of Example 1;

FIG. 5 shows the DSC chart of the polar group-containing olefincopolymer 1 of Example 1;

FIG. 6 shows the ¹H-NMR measurement result of the polar group-containingolefin copolymer 9 of Example 9;

FIG. 7 shows the ¹H-NMR measurement result of the polar group-containingolefin copolymer 10 of Example 10;

FIG. 8 shows the ¹H-NMR measurement result of the polar group-containingolefin copolymer 11 of Example 11;

FIG. 9 shows the ¹H-NMR measurement result of the polar group-containingolefin copolymer 12 of Example 12;

FIG. 10 shows the UC-NMR measurement result of the polargroup-containing olefin copolymer 13 of Example 13;

FIG. 11 shows the UC-NMR measurement result of the polargroup-containing olefin copolymer 14 of Example 14;

FIG. 12 shows the ¹H-NMR measurement result of the polargroup-containing olefin copolymer 15 of Example 15;

FIG. 13 shows the UC-NMR measurement result of the polargroup-containing olefin copolymer 15 of Example 15;

FIG. 14 shows the structures of α and β shown in FIG. 1;

FIG. 15 is a schematic view of the structure of the polargroup-containing olefin copolymer of the present disclosure;

FIG. 16 is a schematic view of the structure of a conventionalethylene-acrylic acid ester copolymer; and

FIG. 17 is a schematic view of a conventional ethylene-carbon monoxidecopolymer.

DESCRIPTION OF EMBODIMENTS

Hereinafter, the polar group-containing olefin copolymer of the presentdisclosure is explained in detail. In the present Description,“(meth)acrylic acid” denotes “acrylic acid” or “methacrylic acid”, and“(meth)acryloyl” denotes “acryloyl” or “methacryloyl”. Also in thepresent Description, “to” which shows a numerical range is used todescribe a range in which the numerical values described before andafter “to” indicate the lower limit value and the upper limit value.

The polar group-containing olefin copolymer of the present disclosure isa polar group-containing olefin copolymer comprising a structural unit(A) derived from one or more monomers selected from the group consistingof ethylene and an olefin containing 3 to 20 carbon atoms, and astructural unit (B) represented by the following general formula (I):

where R^(x) and R^(y) are each independently a hydrogen atom, a halogenatom, a hydroxyl group, a formyl group, an ester group containing 1 to30 carbon atoms, an acyloxy group containing 1 to 30 carbon atoms, anacyl group containing 1 to 30 carbon atoms, an alkoxy group containing 1to 30 carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, analkylthio group containing 1 to 30 carbon atoms, an arylthio groupcontaining 6 to 30 carbon atoms, a nitro group, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or R^(x) and R^(y) are optionally bound to each other toform a 4- to 10-membered ring.

As shown in FIG. 15, the polar group-containing olefin copolymer of thepresent disclosure is a novel, multi-component polar group-containingolefin copolymer in which an enone structure, which is an unsaturatedbond structure forming the conjugated system of alkene and ketone, iscontained in the main chain of the polymer as the structural unit (B).

Since the enone structure has very high reactivity, the polargroup-containing olefin copolymer of the present disclosure is usable asthe substrate for reactions such as the Michael addition reaction andthe Knoevenagel condensation reaction. Since the enone structure isknown to show reactivity to anionic polymerization and radicalpolymerization, the polar group-containing olefin copolymer of thepresent disclosure is also usable as a polymerizable monomer.

In the polar group-containing olefin copolymer of the presentdisclosure, when a functional group different from a hydrogen atom iscontained in the unsaturated bond of the enone structure, there is apossibility that the functional group functions as a leaving group. Whenthe functional group functions as a leaving group, it can be thestarting point for introducing a different substituent by using thepolar group-containing olefin copolymer in the Heck reaction, the Wackerreaction, etc.

As described above, the polar group-containing olefin copolymer of thepresent disclosure is expected to be a raw material that can betransformed into various composite materials.

Also, the polar group-containing olefin copolymer of the presentdisclosure can contain two functional groups in the unsaturated bond ofthe enone structure, and it can contain three functional groups and oneunsaturated bond always in the same sequence in the structural unit (B).Accordingly, for example, when R^(x) and R^(y) are groups containing afunctional group having metal coordination properties, the polargroup-containing olefin copolymer of the present disclosure is expectedto function as a functional substance having chelate coordinationproperties with metal complexes, etc. Due to this function, the polargroup-containing olefin copolymer of the present disclosure is alsoexpected to be usable as a carrier for metal complex catalysts, anadsorbent for metal complex recovery, etc.

(1) Structural Unit (A)

The structural unit (A) is a structural unit derived from one or moremonomers (A) selected from the group consisting of ethylene and anolefin containing 3 to 20 carbon atoms. The monomer (s) (A) used in thepresent disclosure is at least one selected from the group consisting ofethylene and an olefin containing 3 to 20 carbon atoms. The olefincontaining 3 to 20 carbon atoms may be a chain olefin or a cyclicolefin, and it may be at least one selected from the group consisting ofan α-olefin containing 3 to 20 carbon atoms and a cyclic olefincontaining 4 to 20 carbon atoms.

In the present disclosure, the α-olefin containing 3 to 20 carbon atomsis an α-olefin which contains 3 to 20 carbon atoms and which isrepresented by the following structural formula: CH₂═CHR¹⁸ (where R¹⁸ isa hydrocarbon group containing 1 to 18 carbon atoms and optionallyhaving a straight or branched chain structure). The α-olefin containing3 to 20 carbon atoms is more preferably an α-olefin containing 3 to 12carbon atoms.

As the cyclic olefin containing 4 to 20 carbon atoms, examples include,but are not limited to, cyclobutene, cyclopentene, cyclohexene andnorbornene.

As the monomer(s) (A), concrete examples include, but are not limitedto, ethylene, propylene, 1-butene, 1-pentene, 1-hexene, 1-octene,1-decene, 3-methyl-1-butene, 4-methyl-1-pentene and norbornene. From theviewpoint of polymer production efficiency, the monomer (s) (A) ispreferably one or more selected from the group consisting of ethylene,propylene, 1-butene and norbornene, and it is more preferably ethylene.

The structural unit (A) may be one kind of structural unit, or it may betwo or more kinds of structural units.

As the combination of two kinds of structural units, examples include,but are not limited to, structural units derived fromethylene-propylene, ethylene-1-butene, ethylene-1-hexene,ethylene-1-octene, propylene-1-butene, propylene-1-hexene,propylene-1-octene and ethylene-norbornene.

As the combination of three kinds of structural units, examples include,but are not limited to, structural units derived fromethylene-propylene-1-butene, ethylene-propylene-1-hexene,ethylene-propylene-1-octene, propylene-1-butene-hexene, andpropylene-1-butene-1-octene.

In the present disclosure, the monomer(s) (A) used in the structuralunit (A) preferably contains ethylene as an essential component. Asneeded, the monomer(s) (A) may further contain one or more kinds ofα-olefins each of which contains 3 to 20 carbon atoms.

The ethylene in the monomer (s) (A) may be from 65 mol % to 100 mol %,or may be from 70 mol % to 100 mol %, for the total 100 mol % of themonomer(s) (A).

(2) Structural Unit (B)

The structural unit (B) is a structural unit represented by thefollowing general formula (I):

where R^(x) and R^(y) are each independently a hydrogen atom, a halogenatom, a hydroxyl group, a formyl group, an ester group containing 1 to30 carbon atoms, an acyloxy group containing 1 to 30 carbon atoms, anacyl group containing 1 to 30 carbon atoms, an alkoxy group containing 1to 30 carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, analkylthio group containing 1 to 30 carbon atoms, an arylthio groupcontaining 6 to 30 carbon atoms, a nitro group, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or R^(x) and R^(y) are optionally bound to each other toform a 4- to 10-membered ring.

As the halogen atom in the general formula (I), examples include afluorine atom, a chlorine atom, a bromine atom and an iodine atom.

In the general formula (I), the ester group containing 1 to 30 carbonatoms is a monovalent group represented by —COOR^(a) where R^(a) is ahydrocarbon group containing 1 to 30 carbon atoms. The number of thecarbon atoms of the ester group does not include the number of thecarbon atoms of a carbonyl group, and it is the number of the carbonatoms of R^(a). The lower limit may be 1 or more, or it may be 2 ormore. The upper limit may be 30 or less, may be 20 or less, or may be 10or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(a),examples include, but are not limited to, a linear, branched or cyclic,saturated or unsaturated aliphatic hydrocarbon group, an aromatichydrocarbon group, and combinations thereof. Preferred examples include,but are not limited to, an alkenyl group such as an ethenyl group, apropenyl group, a butenyl group and a pentenyl group; an aryl group suchas a phenyl group, a methylphenyl group, an n-propylphenyl group, ani-propylphenyl group, an n-butylphenyl group, an i-butylphenyl group, ans-butylphenyl group, a t-butylphenyl group, an n-hexylphenyl group, atrimethylphenyl group, a pentamethylphenyl group, a biphenyl group, anaphthyl group, an anthracenyl group, a fluorenyl group and a tolylgroup; an aralkyl group such as a benzyl group, a phenylethyl group, aphenylpropyl group, a naphthylmethyl group, a diphenylmethyl group and atriphenylmethyl group; and the following alkyl groups containing 1 to 30carbon atoms.

The alkyl group containing 1 to 30 carbon atoms may be linear, branchedor cyclic. As the alkyl group containing 1 to 30 carbon atoms, preferredexamples include, but are not limited to, a methyl group, an ethylgroup, a 1-propyl group, a 1-butyl group, a 1-pentyl group, a 1-hexylgroup, a 1-heptyl group, a 1-octyl group, a 1-nonyl group, a 1-decylgroup, a t-butyl group, a tricyclohexylmethyl group, an isopropyl group,a 1-dimethylpropyl group, a 1,1,2-trimethylpropyl group, a1,1-diethylpropyl group, an isobutyl group, a 1,1-dimethylbutyl group, a2-pentyl group, a 3-pentyl group, a 2-hexyl group, a 3-hexyl group, a2-ethylhexyl group, a 2-heptyl group, a 3-heptyl group, a 4-heptylgroup, a 2-propylheptyl group, a 2-octyl group, a 3-nonyl group, acyclopropyl group, a cyclobutyl group, a cyclopentyl group, amethylcyclopentyl group, a cyclohexyl group, a methylcyclohexyl group, acycloheptyl group, a cyclooctyl group, a cyclododecyl group, a1-adamantyl group, a 2-adamantyl group and a norbornyl group.

The hydrocarbon group may further contain a substituent. As thesubstituent, examples include, but are not limited to, a halogen atom,an epoxy group, an amino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an alkoxy groupcontaining 1 to 30 carbon atoms, an aryloxy group containing 6 to 30carbon atoms, and a hydroxyl group. The number of carbon atoms containedin the substituent is not included in the above-mentioned number of thecarbon atoms.

The hydrocarbon group as R^(a) is preferably a hydrocarbon groupcontaining 1 to 8 carbon atoms, more preferably a hydrocarbon groupcontaining 1 to 6 carbon atoms, and still more preferably anunsubstituted hydrocarbon group containing 1 to 6 carbon atoms.

As the ester group containing 1 to 30 carbon atoms, preferred examplesinclude, but are not limited to, a methoxycarbonyl group, anethoxycarbonyl group, an n-propoxycarbonyl group, an isopropoxycarbonylgroup, an n-butoxycarbonyl group, a t-butoxycarbonyl group, acyclohexyloxycarbonyl group, a 2-ethylhexyloxycarbonyl group, abenzyloxycarbonyl group and a phenoxycarbonyl group.

In the general formula (I), the acyloxy group containing 1 to 30 carbonatoms is a monovalent group represented by —OCOR^(b) where R^(b) is ahydrocarbon group containing 1 to 30 carbon atoms. The number of thecarbon atoms of the acyloxy group does not include the number of thecarbon atoms of a carbonyl group, and it is the number of the carbonatoms of R^(b). The lower limit may be 1 or more, or it may be 2 ormore. The upper limit may be 30 or less, may be 20 or less, or may be 10or less.

As the hydrocarbon group containing 1 to 30 carbon atoms, examplesinclude those exemplified above as R^(a).

As the acyloxy group containing 1 to 30 carbon atoms, preferred examplesinclude, but are not limited to, an acetyloxy group, a propionyloxygroup, a (meth)acryloyloxy group and a benzoyloxy group.

In the general formula (I), the acyl group containing 1 to 30 carbonatoms is a monovalent group represented by —COR^(c) where R^(c) is ahydrocarbon group containing 1 to 30 carbon atoms. The number of thecarbon atoms of the acyl group does not include the number of the carbonatoms of a carbonyl group, and it is the number of the carbon atoms ofR^(c). The lower limit may be 1 or more, or it may be 2 or more. Theupper limit may be 30 or less, may be 20 or less, or may be 10 or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(c),examples include those exemplified above as R^(a).

As the acyl group containing 1 to 30 carbon atoms, preferred examplesinclude, but are not limited to, an acetyl group, a propionyl group, a(meth)acryloyl group and a benzoyl group.

In the general formula (I), the alkoxy group containing 1 to 30 carbonatoms is a monovalent group represented by —OR^(d) where R^(d) is analkyl group containing 1 to 30 carbon atoms or an aralkyl groupcontaining 7 to 30 carbon atoms. For the number of the carbon atoms ofthe alkoxy group, the lower limit may be 1 or more, or it may be 2 ormore. The upper limit may be 30 or less, may be 20 or less, or may be 10or less.

As the alkyl group containing 1 to 30 carbon atoms and the aralkyl groupcontaining 7 to 30 carbon atoms as R^(d), examples include thoseexemplified above as R^(a).

As the alkoxy group containing 1 to 30 carbon atoms, preferred examplesinclude, but are not limited to, a methoxy group, an ethoxy group, ann-propoxy group, an i-propoxy group, an n-butoxy group, an i-butoxygroup, an s-butoxy group, a t-butoxy group, an n-pentoxy group, ann-hexoxy group, a cyclopropoxy group, a cyclopentoxy group, acyclohexyloxy group, an n-octyloxy group, an n-decyloxy group and abenzyloxy group.

The aryloxy group containing 6 to 30 carbon atoms is a monovalent grouprepresented by —OR^(d′) where R^(d′) is an aryl group containing 6 to 30carbon atoms. For the number of the carbon atoms of the aryl group, thelower limit may be 6 or more, or it may be 8 or more. The upper limitmay be 30 or less, may be 20 or less, or may be 12 or less.

As the aryl group containing 6 to 30 carbon atoms as R^(d′), examplesinclude those corresponding to the aryl group containing 6 to 30 carbonatoms among the examples mentioned above as R^(a).

As the aryloxy group containing 6 to 30 carbon atoms, concrete examplesinclude, but are not limited to, a phenoxy group, a methylphenoxy group,an ethylphenoxy group, a butylphenoxy group, a naphthyloxy group, afluorenyloxy group and an anthracenyloxy group.

In the general formula (I), the alkylthio group containing 1 to 30carbon atoms is a monovalent group represented by —SR where R^(e) is analkyl group containing 1 to 30 carbon atoms or an aralkyl groupcontaining 7 to 30 carbon atoms. For the number of the carbon atoms ofthe alkylthio group, the lower limit may be 1 or more, or it may be 2 ormore. The upper limit may be 30 or less, may be 20 or less, or may be 10or less.

As the alkyl group containing 1 to 30 carbon atoms and the aralkyl groupcontaining 7 to 30 carbon atoms as R^(e), examples include thoseexemplified above as R^(a).

As the alkylthio group containing 1 to 30 carbon atoms, preferredexamples include, but are not limited to, a methylthio group, anethylthio and a benzylthio group.

The arylthio group containing 6 to 30 carbon atoms is a monovalent grouprepresented by —SR^(e′) where R^(e′) is an aryl group containing 6 to 30carbon atoms. For the number of the carbon atoms of the aryl group, thelower limit may be 6 or more, or it may be 8 or more. The upper limitmay be 30 or less, may be 20 or less, or may be 12 or less.

As the aryl group containing 6 to 30 carbon atoms as R^(e′), examplesinclude those corresponding to the aryl group containing 6 to 30 carbonatoms among the examples mentioned above as R^(a).

As the arylthio group containing 6 to 30 carbon atoms, concrete examplesinclude, but are not limited to, a phenylthio group and a naphthylthiogroup.

In the general formula (I), the amino group optionally being substitutedwith a hydrocarbon group containing 1 to 30 carbon atoms, is amonovalent group represented by —N(R^(f))R^(g) where R^(f) and R^(g) areeach independently a hydrogen atom or a hydrocarbon group containing 1to 30 carbon atoms. For the number of the carbon atoms of thehydrocarbon group substituted to the substituted amino group, the lowerlimit may be 1 or more, or it may be 2 or more. The upper limit may be30 or less, may be 20 or less, or may be 10 or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(f) andR^(g), examples include those exemplified above as R^(a).

As the amino group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, preferred examples include, but are notlimited to, an amino group (—NH₂), a monomethylamino group, adimethylamino group, a monoethylamino group, a diethylamino group, amonoisopropylamino group, a diisopropylamino group, a monophenylaminogroup and a diphenylamino group.

In the general formula (I), the silyl group optionally being substitutedwith a hydrocarbon group containing 1 to 30 carbon atoms, is amonovalent group represented by —SiR^(h)R^(i)R^(j) where R^(h), R^(i)and R^(j) are each independently a hydrogen atom or a hydrocarbon groupcontaining 1 to 30 carbon atoms. For the number of the carbon atoms ofthe hydrocarbon group substituted to the silyl group, the lower limitmay be 1 or more, or it may be 2 or more. The upper limit may be 30 orless, may be 20 or less, or may be 10 or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(h), R^(i)and R^(j), examples include those exemplified above as R^(a).

As the silyl group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, preferred examples include, but are notlimited to, a trimethylsilyl group, a triethylsilyl group, atert-butyldimethylsilyl group, a triisopropylsilyl group and atert-butyldiphenylsilyl group.

In the general formula (I), the amide group optionally being substitutedwith a hydrocarbon group containing 1 to 30 carbon atoms is a monovalentgroup represented by —CONR^(k)R^(l) or —NR^(k)COR^(l) where R^(k) andR^(l) are each independently a hydrogen atom or a hydrocarbon groupcontaining 1 to 30 carbon atoms. The number of the carbon atoms of thehydrocarbon group substituted to the substituted amide group, does notinclude the number of the carbon atoms of a carbonyl group, and it isthe number of the carbon atoms of R^(k) and R^(l). The lower limit maybe 1 or more, or it may be 2 or more. The upper limit may be 30 or less,may be 20 or less, or may be 10 or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(k) andR^(l), examples include those exemplified above as R^(a). As the amidegroup optionally being substituted with a hydrocarbon group containing 1to 30 carbon atoms, preferred examples include, but are not limited to,—CONH₂, —CONH(CH₃), —CON(CH₃)₂, —CONH(C₂H₅), —CON(C₂H₅)₂, —CONH(i-C₃H₇), —CON (i-C₃H₇)₂, —CONH(Ph), —CON(Ph)₂, —NHCOCH₃ and —NHCOC₂H₅.In the present Description, “Ph” denotes a phenyl group.

In the general formula (I), the halogen-substituted hydrocarbon groupcontaining 1 to 30 carbon atoms is a group such that at least onehydrogen atom of a hydrocarbon group containing 1 to 30 carbon atoms issubstituted with a halogen atom. As the hydrocarbon group containing 1to 30 carbon atoms, examples include those exemplified above as R^(a).Of them, an alkyl group and an aryl group are preferred from theviewpoint of availability. As the halogen atom, examples include afluorine atom, a chlorine atom, a bromine atom and an iodine atom.

For the number of the carbon atoms of the halogen-substitutedhydrocarbon group containing 1 to 30 carbon atoms, the lower limit maybe 1 or more, or it may be 2 or more. The upper limit may be 30 or less,may be 20 or less, or may be 10 or less.

As the halogen-substituted hydrocarbon group containing 1 to 30 carbonatoms, examples include, but are not limited to, a halomethyl group suchthat each of 1 to 3 hydrogen atoms of a methyl group is substituted witha halogen atom, a chloroethyl group, a γ-chloropropyl group, a3,3′,3″-trifluoropropyl group, a perfluoropropyl group, aperfluorophenyl group, a bromophenyl group, a chlorophenyl group, afluorophenyl group and a dichlorophenyl group. As the halomethyl group,examples include, but are not limited to, a chloromethyl group, abromomethyl group, a fluoromethyl group, a dichloromethyl group and atrifluoromethyl group.

In the general formula (I), as the hydrocarbon group containing 1 to 30carbon atoms of the hydrocarbon group containing 1 to 30 carbon atomsand optionally being substituted with a functional group containing atleast one selected from the group consisting of an oxygen atom, a sulfuratom and a nitrogen atom, examples include those exemplified above asR^(a). Of them, from the viewpoint of copolymer production efficiency,an alkyl group, an aryl group or an aralkyl group is preferred as thehydrocarbon group containing 1 to 30 carbon atoms and optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom.

In the general formula (I), the number of the carbon atoms of theheterocyclic ring of the heterocyclic group optionally being substitutedwith a functional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom and a nitrogen atom, is 2 ormore. The upper limit may be 8 or less, 6 or less, or 5 or less.

As the heterocyclic group, examples include, but are not limited to, apyridyl group, a furanyl group, a thienyl group, an oxazolyl group, anoxazolidinyl group, an isoxazolidinyl group, a thiazolyl group, adihydrofuranyl group and a tetrahydrofuranyl group.

As the functional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom and a nitrogen atom,examples include, but are not limited to, a hydroxyl group, a formylgroup, an epoxy group, an ester group containing 1 to 30 carbon atoms,an acyloxy group containing 1 to 30 carbon atoms, an acyl groupcontaining 1 to 30 carbon atoms, an alkoxy group containing 1 to 30carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, a cyanogroup, a nitro group, an amino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, an alkylthio group containing 1 to 30 carbon atoms, anarylthio group containing 6 to 30 carbon atoms, a sulfonyl groupcontaining 1 to 30 carbon atoms, a sulfoxide group containing 1 to 30carbon atoms, and a sulfonic acid ester group containing 1 to 30 carbonatoms.

The ester group containing 1 to 30 carbon atoms, the acyloxy groupcontaining 1 to 30 carbon atoms, the acyl group containing 1 to 30carbon atoms, the alkoxy group containing 1 to 30 carbon atoms, thearyloxy group containing 6 to 30 carbon atoms, the amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, the amide group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, the alkylthio groupcontaining 1 to 30 carbon atoms, and the arylthio group containing 6 to30 carbon atoms may be the same as those described above.

The sulfonyl group containing 1 to 30 carbon atoms is a monovalent grouprepresented by —SO₂R^(m) where R^(m) is a hydrocarbon group containing 1to 30 carbon atoms. For the number of the carbon atoms of the sulfonylgroup, the lower limit may be 1 or more, or it may be 2 or more. Theupper limit may be 30 or less, may be 20 or less, or may be 10 or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(m),examples include those exemplified above as R^(a).

As the sulfonyl group containing 1 to 30 carbon atoms, preferredexamples include, but are not limited to, —SO₂CH₃ and —SO₂Ph.

The sulfoxide group containing 1 to 30 carbon atoms is a monovalentgroup represented by —SOR^(n) where R^(n) is a hydrocarbon groupcontaining 1 to 30 carbon atoms. For the number of the carbon atoms ofthe sulfoxide group, the lower limit may be 1 or more, or it may be 2 ormore. The upper limit may be 30 or less, may be 20 or less, or may be 10or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(n),examples include those exemplified above as R^(a).

As the sulfoxide group containing 1 to 30 carbon atoms, preferredexamples include, but are not limited to, —SOCH₃ and —SOPh.

The sulfonic acid ester group containing 1 to 30 carbon atoms is amonovalent group represented by —OSO₂R^(o) where R^(o) is a hydrocarbongroup containing 1 to 30 carbon atoms. For the number of the carbonatoms of the sulfonic acid ester group, the lower limit may be 1 ormore, or it may be 2 or more. The upper limit may be 30 or less, may be20 or less, or may be 10 or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(o),examples include those exemplified above as R^(a).

As the sulfonic acid ester group containing 1 to 30 carbon atoms,preferred examples include, but are not limited to, —SO₃CH₃ and —SO₃Ph.

From the viewpoint of copolymer production efficiency, the functionalgroup containing at least one selected from the group consisting of anoxygen atom, a sulfur atom and a nitrogen atom, is preferably at leastone selected from the group consisting of a hydroxyl group, an alkoxygroup containing 1 to 30 carbon atoms, an aryloxy group containing 6 to30 carbon atoms, an amino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an alkylthio groupcontaining 1 to 30 carbon atoms and an arylthio group containing 6 to 30carbon atoms. The functional group is more preferably at least oneselected from the group consisting of an alkoxy group containing 1 to 30carbon atoms, an aryloxy group containing 6 to 30 carbon atoms and anamino group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms.

In the general formula (I), R^(x) and R^(y) may be bound to each otherto form a 4- to 10-membered ring in combination with the unsaturatedbond to which R^(x) and R^(y) are bound. The ring formed by R^(x) andR^(y) bound to each other, may be a carbon ring or a heterocyclic ring,and the carbon ring or the heterocyclic ring may be monocyclic orpolycyclic. R^(x) and R^(y) may be bound to each other to form asaturated or unsaturated bond, or they may form a —CO—O—CO— group or anon-aromatic ring.

For the structural unit (B), from the viewpoint of a wider range ofapplications of the polar group-containing olefin copolymer of thepresent disclosure and from the viewpoint of the stability of thecompound represented by the general formula (1), at least one of R^(x)and R^(y) in the general formula (I) is preferably different from ahydrogen atom. That is, at least one of R^(x) and R^(y) is preferably ahalogen atom, a hydroxyl group, a formyl group, an ester groupcontaining 1 to 30 carbon atoms, an acyloxy group containing 1 to 30carbon atoms, an acyl group containing 1 to 30 carbon atoms, an alkoxygroup containing 1 to 30 carbon atoms, an aryloxy group containing 6 to30 carbon atoms, an alkylthio group containing 1 to 30 carbon atoms, anarylthio group containing 6 to 30 carbon atoms, a nitro group, an aminogroup optionally being substituted with a hydrocarbon group containing 1to 30 carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or R^(x) and R^(y) are optionally bound to each other toform a 4- to 10-membered ring.

From the viewpoint of enhancing the applicability of the polargroup-containing olefin copolymer and from the viewpoint of thestability of the compound represented by the general formula (1), it ispreferable that R^(x) and R^(y) are each independently a hydrogen atom,a hydroxyl group, a formyl group, an ester group containing 1 to 30carbon atoms, an acyl group containing 1 to 30 carbon atoms, an alkoxygroup containing 1 to 30 carbon atoms, an amino group optionally beingsubstituted with a hydrocarbon group containing 1 to 30 carbon atoms, asilyl group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, a halogen-substituted hydrocarbon groupcontaining 1 to 30 carbon atoms, or a hydrocarbon group containing 1 to30 carbon atoms and optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom, or R^(x) and R^(y) areoptionally bound to each other to form a 4- to 10-membered ring, and atleast one of R^(x) and R^(y) is different from a hydrogen atom. That is,it is preferable that at least one of R^(x) and R^(y) is a hydroxylgroup, a formyl group, an ester group containing 1 to 30 carbon atoms,an acyl group containing 1 to 30 carbon atoms, an alkoxy groupcontaining 1 to 30 carbon atoms, an amino group optionally beingsubstituted with a hydrocarbon group containing 1 to 30 carbon atoms, asilyl group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, a halogen-substituted hydrocarbon groupcontaining 1 to 30 carbon atoms, a hydrocarbon group containing 1 to 30carbon atoms and optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom, or a heterocyclic groupoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or R^(x) and R^(y) are optionally bound to eachother to form a 4- to 10-membered ring.

When at least one of R^(x) and R^(y) is a group different from ahydrogen atom, for example, at least one of R^(x) and R^(y) is thoughtto function as a leaving group. When R^(x) or R^(y) functions as aleaving group, R^(x) or R^(y) can be the starting point for introducinga different substituent when the polar group-containing olefin copolymeris used for the Heck reaction, the Wacker reaction, etc. The group thatfunctions as a leaving group is preferably a functional group containinga polar group, such as a halogen atom and an acyloxy group.

For the structural unit (B), from the viewpoint of enhancing theapplicability of the polar group-containing olefin copolymer of thepresent disclosure, it is preferable that R^(x) and R^(y) in the generalformula (I) are each independently a halogen atom, a hydroxyl group, aformyl group, an ester group containing 1 to 30 carbon atoms, an acyloxygroup containing 1 to 30 carbon atoms, an acyl group containing 1 to 30carbon atoms, an alkoxy group containing 1 to 30 carbon atoms, anaryloxy group containing 6 to 30 carbon atoms, an alkylthio groupcontaining 1 to 30 carbon atoms, an arylthio group containing 6 to 30carbon atoms, an amino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, a silyl groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, an amide group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, a halogen-substitutedhydrocarbon group containing 1 to 30 carbon atoms, a hydrocarbon groupcontaining 1 to 30 carbon atoms and optionally being substituted with afunctional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom and a nitrogen atom, or aheterocyclic group optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom, or R^(x) and R^(y) areoptionally bound to each other to form a 4- to 10-membered ring. It ismore preferable that R^(x) and R^(y) in the general formula (I) are eachindependently a hydroxyl group, a formyl group, an ester groupcontaining 1 to 30 carbon atoms, an acyl group containing 1 to 30 carbonatoms, an alkoxy group containing 1 to 30 carbon atoms, an aryloxy groupcontaining 6 to 30 carbon atoms, an alkylthio group containing 1 to 30carbon atoms, an arylthio group containing 6 to 30 carbon atoms, anamino group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, a silyl group optionally beingsubstituted with a hydrocarbon group containing 1 to 30 carbon atoms, ahalogen-substituted hydrocarbon group containing 1 to 30 carbon atoms, ahydrocarbon group containing 1 to 30 carbon atoms and optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or a heterocyclic group optionally being substituted witha functional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom and a nitrogen atom, orR^(x) and R^(y) are optionally bound to each other to form a 4- to10-membered ring.

It is even more preferable that R^(x) and R^(y) are each independently ahydroxyl group, a formyl group, an ester group containing 1 to 30 carbonatoms, an acyl group containing 1 to 30 carbon atoms, an alkoxy groupcontaining 1 to 30 carbon atoms, an amino group optionally beingsubstituted with a hydrocarbon group containing 1 to 30 carbon atoms, asilyl group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, a halogen-substituted hydrocarbon groupcontaining 1 to 30 carbon atoms, a hydrocarbon group containing 1 to 30carbon atoms and optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom, or a heterocyclic groupoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or R^(x) and R^(y) are optionally bound to eachother to form a 4- to 10-membered ring. It is still more preferable thatR^(x) and R^(y) are each independently a formyl group, an ester groupcontaining 1 to 30 carbon atoms, an acyl group containing 1 to 30 carbonatoms, an alkoxy group containing 1 to 30 carbon atoms, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, a halogen-substitutedhydrocarbon group containing 1 to 30 carbon atoms, a hydrocarbon groupcontaining 1 to 30 carbon atoms and optionally being substituted with afunctional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom and a nitrogen atom, or aheterocyclic group optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom. It is yet more preferable thatR^(x) and R^(y) are each independently an alkoxy group containing 1 to30 carbon atoms, an amino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, a silyl groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom.

When R^(x) and R^(y) are each independently a group different from ahydrogen atom, the polar group-containing olefin copolymer of thepresent disclosure contains three functional groups and one unsaturatedbond always in the same sequence in the structural unit (B).Accordingly, for example, when the functional group is a polarfunctional group having metal coordination properties, the polargroup-containing olefin copolymer of the present disclosure is expectedto function as a functional substance having chelate coordinationproperties with metal complexes, etc. Due to this function, the polargroup-containing olefin copolymer of the present disclosure is alsoexpected to be usable as a carrier for metal complex catalysts, anadsorbent for metal complex recovery, etc. As the polar functional grouphaving metal coordination properties as R^(x) and R^(y), preferredexamples include, but are not limited to, a hydroxyl group that can be aβ-keto-enolate ligand, an amino group that can be a β-keto-iminatoligand, an alkoxy group, an aryloxy group, an alkylthio group, anarylthio group, a halogen atom, and a hydrocarbon group containing 1 to30 carbon atoms and being substituted with these functional groups.

When the polar group-containing olefin copolymer of the presentdisclosure contains three functional groups and one unsaturated bondalways in the same sequence in the structural unit (B), there is apossibility that such a structural unit has various resonancestructures, and the polar group-containing olefin copolymer of thepresent disclosure is expected to be usable in pigments, dyes,medicines, etc.

R^(x) and R^(y) in the general formula (I) may be the same or different.

As the structural unit which is represented by the general formula (I)and which contains three functional groups and one unsaturated bond,examples include, but are not limited to, the following structuralunits.

From the viewpoint of copolymer production efficiency, the structuralunit (B) represented by the general formula (I) is preferably astructural unit derived from one or more monomers (B) selected from thegroup consisting of polar group-containing monomers represented by thefollowing general formula (1), since the structural unit (B) can beintroduced into the copolymer by one-step polymerization reaction. Thepolar group-containing monomer (s) represented by the general formula(1) is ring-opened in the polymerization reaction and incorporated intothe main chain of the polymer to be the structural unit (B).

where R^(x) and R^(y) are each independently a hydrogen atom, a halogenatom, a hydroxyl group, a formyl group, an ester group containing 1 to30 carbon atoms, an acyloxy group containing 1 to 30 carbon atoms, anacyl group containing 1 to 30 carbon atoms, an alkoxy group containing 1to 30 carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, analkylthio group containing 1 to 30 carbon atoms, an arylthio groupcontaining 6 to 30 carbon atoms, a nitro group, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or R^(x) and R^(y) are optionally bound to each other toform a 4- to 10-membered ring.

R^(x) and R^(y) in the general formula (1) are the same as theabove-described R^(x) and R^(y) in the general formula (I).

As the polar group-containing monomer represented by the general formula(1), for example, 2,3-diarylcyclopropen-1-one,2,3-diheteroarylcyclopropen-1-one, 2,3-dialkylcyclopropen-1-one, and2-alkyl-3-arylcyclopropen-1-one are preferably used.

As the 2,3-diarylcyclopropen-1-one and2,3-diheteroarylcyclopropen-1-one, examples include, but are not limitedto, compounds having the following structures.

As the 2,3-dialkylcyclopropen-1-one, examples include, but are notlimited to, compounds having the following structures.

As other compounds in each of which R^(x) and R^(y) in the generalformula (1) are each independently a hydrogen atom, a halogen atom, ahydroxyl group, a formyl group, an ester group containing 1 to 30 carbonatoms, an acyloxy group containing 1 to 30 carbon atoms, an acyl groupcontaining 1 to 30 carbon atoms, an alkoxy group containing 1 to 30carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, analkylthio group containing 1 to 30 carbon atoms, an arylthio groupcontaining 6 to 30 carbon atoms, a nitro group, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, examples include, but are not limited to, compoundshaving the following structures.

As the compound in which R^(x) and R^(y) in the general formula (1) forma ring structure, examples include, but are not limited to, compoundshaving the following structures.

The one or more monomers (B) selected from the group consisting of polargroup-containing monomers represented by the general formula (1) can beproduced by appropriately combining conventionally-known productionmethods. For example, the following production methods can be used: aproduction method by the reaction of various types of alkynes,dichlorocarbene precursors and water (J. Am. Chem. Soc. 1966, 88(3),504-509), a production method by introducing a substituent by the actionof an electrophile on various types of cyclopropenone acetals(Tetrahedron 1992, 48(11), 2045-2057), a production method byisomerizing various types of cyclobutenediones by light to derive them(J. Am. Chem. Soc. 1976, 98(12), 3641-3644) and a production method byclosing a 3-membered ring by debromination of a 1,3-dibromo-2-propanonestructure (J. Am. Chem. Soc. 1965, 87(6), 1326-1331).

As the one or more monomers (B) selected from the group consisting ofpolar group-containing monomers represented by the general formula (1),commercially-available products may be used.

(3) Structural Unit (C)

The structural unit (C) is a structural unit derived from one or moremonomers (C) selected from the group consisting of a polargroup-containing monomer (c-1) represented by the following generalformula (2) and a polar group-containing monomer (c-2) represented bythe following general formula (3):

where R¹ and R² are each independently a hydrogen atom, an ester groupcontaining 1 to 30 carbon atoms, an acyloxy group containing 1 to 30carbon atoms, an alkoxy group containing 1 to 30 carbon atoms, anaryloxy group containing 6 to 30 carbon atoms, a cyano group, an aminogroup optionally being substituted with a hydrocarbon group containing 1to 30 carbon atoms, an amide group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an imino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, or a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atom,a nitrogen atom and a phosphorus atom, and at least one of R¹ and R² isa group containing at least one of an oxygen atom and a nitrogen atom,and

where R³ to R¹⁰ are each independently a hydrogen atom, a halogen atomor a hydrocarbon group containing 1 to 20 carbon atoms; n is 0 or apositive integer, and when n is 2 or more, R⁷ to R¹⁰ are each optionallythe same or different in each repeating unit; R¹¹ to R¹⁴ are eachindependently a hydrogen atom, an ester group containing 1 to 30 carbonatoms, an acyloxy group containing 1 to 30 carbon atoms, an alkoxy groupcontaining 1 to 30 carbon atoms, an aryloxy group containing 6 to 30carbon atoms, a cyano group, an amino group optionally being substitutedwith a hydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, an imino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, or a hydrocarbongroup containing 1 to 30 carbon atoms and optionally being substitutedwith a functional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom, a nitrogen atom and aphosphorus atom, and at least one of R¹¹ to R¹⁴ is a group containing atleast one of an oxygen atom and a nitrogen atom; and R¹¹ and R¹² areoptionally integrated to form a divalent organic group, and R¹³ and R¹⁴are optionally integrated to form a divalent organic group; R¹¹ or R¹²optionally forms a ring with R¹³ or R¹⁴.(3-1) Polar Group-Containing Monomer (c-1)

In the general formula (2), the ester group containing 1 to 30 carbonatoms, the acyloxy group containing 1 to 30 carbon atoms, the alkoxygroup containing 1 to 30 carbon atoms, the aryloxy group containing 6 to30 carbon atoms, the amino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, the amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, the imino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, and thehalogen-substituted hydrocarbon group containing 1 to 30 carbon atomsmay be the same as those described above for the general formula (I).

Also in the general formula (2), among hydrocarbon groups containing 1to 30 carbon atoms and optionally being substituted with a functionalgroup containing at least one selected from the group consisting of anoxygen atom, a sulfur atom, a nitrogen atom and a phosphorus atom, thehydrocarbon group containing 1 to 30 carbon atoms and optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, may be the same as that described above for the generalformula (I).

As the hydrocarbon group containing 1 to 30 carbon atoms of thehydrocarbon group containing 1 to 30 carbon atoms and optionally beingsubstituted with a functional group containing a phosphorus atom,examples include those exemplified above as R^(a).

As the functional group containing a phosphorus atom, examples include,but are not limited to, a phosphite group containing 1 to 30 carbonatoms, a phosphate group containing 1 to 30 carbon atoms, and aphosphorus ylide group containing 1 to 30 carbon atoms.

The phosphite group containing 1 to 30 carbon atoms is a monovalentgroup represented by —P(OR^(p))₂ where R^(p) is each independently ahydrocarbon group containing 1 to 30 carbon atoms. For the number of thecarbon atoms of the phosphite group, the lower limit may be 1 or more,or it may be 2 or more. The upper limit may be 30 or less, may be 20 orless, or may be 10 or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(p),examples include those exemplified above as R^(a). As the phosphitegroup containing 1 to 30 carbon atoms, preferred examples include, butare not limited to, —P(OPh)₂ and —P(OCH₃)₂.

The phosphate group containing 1 to 30 carbon atoms is a monovalentgroup represented by —P(═O) (OR^(q))₂ where R^(q) is each independentlya hydrocarbon group containing 1 to 30 carbon atoms. For the number ofthe carbon atoms of the phosphate group, the lower limit may be 1 ormore, or it may be 2 or more. The upper limit may be 30 or less, may be20 or less, or may be 10 or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(q),examples include those exemplified above as R^(a). As the phosphategroup containing 1 to 30 carbon atoms, preferred examples include, butare not limited to, —P(═O) (OPh)₂ and —P(═O) (OCH₃) 2.

The phosphorus ylide group containing 1 to 30 carbon atoms is amonovalent group represented by —P═CR^(r)R^(s) where R^(r) and R^(s) areeach independently a hydrogen atom or a hydrocarbon group containing 1to 30 carbon atoms and at least one is the hydrocarbon group. The numberof the carbon atoms of the hydrocarbon group substituted to thephosphorus ylide group, does not include the number of the carbon atomsof P═C, and it is the number of the carbon atoms of R^(r) or R^(s). Thelower limit may be 1 or more, or it may be 2 or more. The upper limitmay be 30 or less, may be 20 or less, or may be 10 or less.

As the hydrocarbon group containing 1 to 30 carbon atoms as R^(r) andR^(s), examples include those exemplified above as R^(a).

As the phosphorus ylide group containing 1 to 30 carbon atoms, preferredexamples include, but are not limited to, —P═CHCH₃, —P═CHPh and—P═CHCH₂Ph.

At least one of R¹ and R² is a group containing at least one of anoxygen atom and a nitrogen atom. As the group containing at least one ofan oxygen atom and a nitrogen atom, examples include an ester groupcontaining 1 to 30 carbon atoms, an acyloxy group containing 1 to 30carbon atoms, an alkoxy group containing 1 to 30 carbon atoms, anaryloxy group containing 6 to 30 carbon atoms, a cyano group, an aminogroup optionally being substituted with a hydrocarbon group containing 1to 30 carbon atoms, an amide group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an imino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, and a hydrocarbon group containing 1 to 30 carbon atomsand being substituted with a substituent containing at least one of anoxygen atom and a nitrogen atom. As the substituent containing at leastone of an oxygen atom and a nitrogen atom of the hydrocarbon groupcontaining 1 to 30 carbon atoms, examples include, but are not limitedto, a hydroxyl group, an epoxy group, an ester group containing 1 to 30carbon atoms, an acyloxy group containing 1 to 30 carbon atoms, analkoxy group containing 1 to 30 carbon atoms, an aryloxy groupcontaining 6 to 30 carbon atoms, a cyano group, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, an amide group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an imino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a thioester group containing 1 to 30 carbon atoms, asulfonyl group containing 1 to 30 carbon atoms, a sulfoxide groupcontaining 1 to 30 carbon atoms, a sulfonic acid ester group containing1 to 30 carbon atoms, a phosphite group containing 1 to 30 carbon atoms,and a phosphate group containing 1 to 30 carbon atoms.

As the polar group-containing monomer (c-1) represented by the generalformula (2), for example, a (meth)acrylic acid ester is preferably used.

As the (meth)acrylic acid ester, examples include, but are not limitedto, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl(meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate,isobutyl (meth)acrylate, t-butyl (meth)acrylate, pentyl (meth)acrylate,hexyl (meth)acrylate, cyclohexyl (meth)acrylate, octyl (meth)acrylate,2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate,dodecyl (meth)acrylate, phenyl (meth)acrylate, toluyl (meth)acrylate,benzyl (meth)acrylate, hydroxyethyl (meth)acrylate, hydroxybutyl(meth)acrylate, 1,4-cyclohexanedimethanol mono(meth)acrylate,4-hydroxybutyl (meth)acrylate glycidyl ether, polyethylene glycol(meth)acrylate ester, dimethylaminoethyl (meth)acrylate,diethylaminoethyl (meth)acrylate, 2-aminoethyl (meth)acrylate,2-methoxyethyl (meth)acrylate, 3-methoxypropyl (meth)acrylate, glycidyl(meth)acrylate, trifluoromethyl (meth)acrylate, 2-trifluoromethylethyl(meth)acrylate, perfluoroethyl (meth)acrylate, and4-(1,2,2,6,6-pentamethylpiperidyl) acrylate.

As the polar group-containing monomer (c-1) represented by the generalformula (2), examples include, but are not limited to, (meth)acrylamide,(meth)acrylonitrile, vinylamide, vinyl acetate, allyl acetate, 3-butenylacetate, 3-cyanopropene, methyl vinyl ether, 3-chloropropene,N-propylidene ethenamine, 3-(methylthio)-1-propene,3-(methylsulfinyl)-1-propene, 3-(methylsulfonyl)-1-propene,2-propene-1-sulfonic acid methyl ester, and 2-propenylphosphonic aciddimethyl ester.

In the general formula (2), R¹ is preferably a hydrogen atom, from theviewpoint of polymer production efficiency, polymer molecular weight,and copolymerizability with the monomers (A) and (B).

Also in the general formula (2), it is preferable that R¹ is a hydrogenatom, and R² is an ester group containing 1 to 30 carbon atoms, a cyanogroup, a cyanomethyl group, a cyanoethyl group, a halomethyl group, anacyloxymethyl group or an acyloxyethyl group, from the viewpoint ofpolymer production efficiency, polymer molecular weight, andcopolymerizability with the monomers (A) and (B).

The polar group-containing monomer (c-1) represented by the generalformula (2) is preferably at least one selected from the groupconsisting of methyl acrylate, ethyl acrylate, propyl acrylate, butylacrylate, vinyl acetate, allyl acetate, 3-butenyl acetate, acrylonitrileand 3-cyanopropene, from the following viewpoint: high weight ratio ofthe heteroatom; few side effects on late transition metal catalysts;polymer production efficiency; polymer molecular weight; andcopolymerizability with the monomers (A) and (B).

(3-2) Polar Group-Containing Monomer (c-2)

As the halogen atom as R³ to R¹⁰ in the general formula (3), examplesinclude a fluorine atom, a chlorine atom and a bromine atom.

As the hydrocarbon group containing 1 to 20 carbon atoms as R³ to R¹⁰,examples include those exemplified above as R^(a) in the general formula(I), such as an alkyl group such as a methyl group, an ethyl group and apropyl group; a cycloalkyl group such as a cyclopentyl group and acyclohexyl group; and an alkenyl group such as a vinyl group, an allylgroup and a propenyl group.

In the general formula (3), “n” is 0 or a positive integer. It ispreferably 2 or less, and more preferably 1 or less.

As R¹¹ to R¹⁴ in the general formula (3), the ester group containing 1to 30 carbon atoms, the acyloxy group containing 1 to 30 carbon atoms,the alkoxy group containing 1 to 30 carbon atoms, the amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, the amide group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, the imino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, or the hydrocarbon group containing 1 to 30 carbon atomsand optionally being substituted with a functional group containing atleast one selected from the group consisting of an oxygen atom, a sulfuratom, a nitrogen atom and a phosphorus atom, may be the same as thosedescribed above as R¹ and R² in the general formula (2).

In the general formula (3), at least one of R¹¹ to R¹⁴ is a groupcontaining at least one of an oxygen atom and a nitrogen atom. The groupcontaining at least one of an oxygen atom and a nitrogen atom may be thesame as those described above as R¹ and R² in the general formula (2).

R¹¹ and R¹² are optionally integrated to form a divalent organic group,and R¹³ and R¹⁴ are optionally integrated to form a divalent organicgroup. The organic group means a group containing at least a carbonatom. When each of them is integrated to form a divalent organic group,it is preferably a divalent hydrocarbon group, and the hydrocarbon groupmay contain a linking group such as —CO—, —O(CO)—, —COO—, —C(═O)OC(═O)—, —C(═O) NR^(f)C(═O)— (where R^(f) is as described above), —SO₂—and —O—.

R¹¹ or R¹² is optionally bound to each other with R¹³ or R¹⁴ to form aring. They may form a carbon ring or heterocyclic ring, and the carbonring or heterocyclic ring may be monocyclic or polycyclic. For example,R¹¹ or R¹² is optionally bound to each other with R¹³ or R¹⁴ to form a—CO—O—CO— group.

In the general formula (3), from the viewpoint of ease of synthesizingthe polar monomer itself, n is preferably 0 or 1, and R³ to R¹⁰ arepreferably a hydrogen atom or methyl group.

From the viewpoint of few side effects on late transition metalcatalysts, polymer production efficiency, polymer molecular weight, andcopolymerizability with the monomers (A) and (B), the polargroup-containing monomer (c-2) represented by the general formula (3) ispreferably at least one selected from the group consisting of methyl5-norbornene-2-carboxylate, ethyl 5-norbornene-2-carboxylate, propyl5-norbornene-2-carboxylate, butyl 5-norbornene-2-carboxylate, dimethyl5-norbornene-2,3-dicarboxylate, 5-norbornene-2,3-dicarboxylic anhydride,2-hydroxy-5-norbornene, 5-norbornene-2-methanol,5-norbornene-2-methylamine, 2-acetoxy-5-norbornene,2-cyanomethyl-5-norbornene, and 5-norbornene-2-carbonitrile. Also, thepolar group-containing monomer (c-2) is more preferably at least oneselected from the group consisting of methyl 5-norbornene-2-carboxylate,ethyl 5-norbornene-2-carboxylate, propyl 5-norbornene-2-carboxylate,butyl 5-norbornene-2-carboxylate, 5-norbornene-2,3-dicarboxylicanhydride, and 5-norbornene-2-methanol.

(4) Other Structural Unit

The polar group-containing olefin copolymer of the present disclosuremay further contain other structural unit different from the structuralunits (A), (B) and (C). As the other structural unit, examples include,but are not limited to, a structural unit represented by the followingformula (II). The structural unit represented by the following formula(II) may be a structural unit derived from the one or more monomers (B)selected from the group consisting of polar group-containing monomersrepresented by the general formula (1).

(5) Polar Group-Containing Olefin Copolymer

The polar group-containing olefin copolymer of the present disclosurecomprises a structural unit (A) derived from one or more monomersselected from the group consisting of ethylene and an olefin containing3 to 20 carbon atoms, and a structural unit (B) represented by thegeneral formula (I).

The polar group-containing olefin copolymer of the present disclosureneeds to contain at least one kind of structural unit (A) and at leastone kind of structural unit (B), and it needs to contain structuralunits derived from a total of two or more kinds of monomers.

In the present disclosure, the percentage of the structural unit (A) inthe polar group-containing olefin copolymer may be appropriatelyselected depending on the desired properties. For the total 100 mol % ofthe structural units, the lower limit is generally 60.00 mol % or more,preferably 65.50 mol % or more, more preferably 76.00 mol % or more,still more preferably 85.00 mol % or more, and particularly preferably87.00 mol % or more. On the other hand, the upper limit is generally99.98 mol % or less, preferably 99.92 mol % or less, more preferably99.90 mol % or less, still more preferably 99.80 mol % or less, and evenmore preferably 99.70 mol % or less.

The percentage of the structural unit (B) in the polar group-containingolefin copolymer may be appropriately selected depending on the averagemolecular weight and the desired properties. For the total 100 mol % ofthe structural units, the lower limit is generally 0.01 mol % or more,preferably 0.05 mol % or more, more preferably 0.10 mol % or more, andstill more preferably 0.20 mol % or more. On the other hand, the upperlimit is generally 15.00 mol % or less, preferably 10.00 mol % or less,more preferably 8.00 mol % or less, and still more preferably 6.00 mol %or less.

The polar group-containing olefin copolymer of the present disclosuremay further comprise one or more structural units (C) derived from oneor more monomers selected from the group consisting of the polargroup-containing monomer (c-1) and the polar group-containing monomer(c-2).

When the polar group-containing olefin copolymer of the presentdisclosure contain the structural unit (C), the percentage of thestructural unit (C) in the polar group-containing olefin copolymer maybe appropriately selected depending on the desired properties. For thetotal 100 mol % of the structural units, the lower limit is generally0.01 mol % or more, preferably 0.05 mol % or more, more preferably 0.10mol % or more, and still more preferably 0.50 mol % or more. On theother hand, the upper limit is generally 35.00 mol % or less, preferably30.00 mol % or less, more preferably 20.00 mol % or less, and still morepreferably 10.00 mol % or less.

The polar group-containing olefin copolymer of the present disclosuremay further contain the structural unit represented by the formula (II).

When the polar group-containing olefin copolymer of the presentdisclosure contain the structural unit represented by the formula (II),the percentage of the structural unit contained in the polargroup-containing olefin copolymer may be appropriately selecteddepending on the desired properties. For the total 100 mol % of thestructural units, the lower limit is generally 0.001 mol % or more, maybe 0.005 mol % or more, or may be 0.01 mol % or more. On the other hand,the upper limit is generally 15.00 mol % or less, preferably 10.00 mol %or less, more preferably 3.00 mol % or less, and still more preferably2.00 mol % or less.

For the total 100 mol % of the structural unit (B) and the structuralunit represented by the formula (II), the percentage of the structuralunit (B) is generally 50 mol % or more, preferably 55 mol % or more, andmore preferably 60 mol % or more.

From the viewpoint of a wider range of applications of the polargroup-containing olefin copolymer, the percentage of the structural unit(B) in the polar group-containing olefin copolymer is preferably largerthan the percentage of the structural unit represented by the formula(II).

The structure derived from one molecule of each monomer is defined asone structural unit in the polar group-containing olefin copolymer.

The percentage by mol (mol %) of each structural unit when the wholestructural units of the polar group-containing olefin copolymer aredefined as 100 mol %, is the structural unit amount.

As the polar group-containing olefin copolymer of the presentdisclosure, examples include, but are not limited to, random, block andgraft copolymers of the structural unit (A), the structural unit (B) andthe optionally contained structural unit (C). Of them, the polargroup-containing olefin copolymer may be the random copolymer since thestructural unit (B) can be contained in large amounts.

In the polar group-containing olefin copolymer of the presentdisclosure, the mol fraction [A] of the structural unit (A), the molfraction [B] of the structural unit (B), and the mol fraction [C] of theoptionally contained structural unit (C) preferably satisfy thefollowing: [A]≥{([A]+[B]+[C])×80%}, in order for the copolymer to alsokeep olefin properties such as hydrophobicity.

The structural unit amounts can be controlled by the selection of thecatalyst, the amounts of the monomers (A), (B) and (C) added forpolymerization, and the pressure and temperature of polymerization. As ameans for increasing the structural unit amounts derived from themonomers (B) and (C) in the copolymer, it is effective to increase theamounts of the monomers (B) and (C) added for polymerization, todecrease olefin pressure in polymerization, and to increase thetemperature of polymerization. For example, it is required to controlthe structural unit amounts within the desired copolymer range byadjusting these factors.

The structural unit amount of the polar group-containing olefincopolymer of the present disclosure is obtained by use of a ¹H-NMRspectrum and a ¹³C-NMR spectrum. The NMR spectrum is measured by thefollowing method.

The polar group-containing olefin copolymer is dissolved by heating in1,1,2,2-tetrachloroethane-d2 to obtain a homogenous solution, and thesolution is subjected to NMR measurement. The ¹H-NMR spectrum is aspectrum for a 5 mass % solution of the polar group-containing olefincopolymer, and the ¹³C-NMR spectrum is a spectrum for a 15 mass %solution of the polar group-containing olefin copolymer.

As another method, about 150 mg of the polar group-containing olefincopolymer may be dissolved by heating in 2.4 mL of a mixed solvent of(1,2-dichlorobenzene:bromobenzene-d5=1:2) to obtain a homogenoussolution, and the homogenous solution may be subjected to NMRmeasurement.

The NMR measurement is carried out at 120° C. using ASCEND 500(manufactured by BRUKER) or AVANCE 400 (manufactured by BRUKER), forexample.

The ¹³C-NMR is measured using chromium(III) acetylacetonate as arelaxation reagent and using an inverse-gated decoupling method (a 90°pulse of 9.0 microseconds, spectral width: 31 kHz, relaxation time: 10seconds, acquisition time: 10 seconds, and accumulated number of timesof FID: 5,000 to 10,000), and then quantitative analysis is performed.Or, the ¹³C-NMR may be measured using an inverse-gated decoupling method(a 90° pulse of 15.8 microseconds, spectral width: 25 kHz, relaxationtime: 50 seconds, acquisition time: 1.5 seconds, and accumulated numberof times of FID: 1,024), and then quantitative analysis is performed.

The weight average molecular weight (Mw) of the polar group-containingolefin copolymer of the present disclosure is in a range of generallyfrom 1,000 to 2,000,000, preferably from 10,000 to 1,500,000, morepreferably from 20,000 to 1,000,000, still more preferably from 31,000to 800,000, and even more preferably from 35,000 to 800,000. If the Mwis less than 1,000, physical properties such as mechanical strength andimpact resistance may be insufficient. If the Mw is more than 2,000,000,the melt viscosity may become very high, and then mold processing may bedifficult.

The number average molecular weight (Mn) of the polar group-containingolefin copolymer of the present disclosure is in a range of generallyfrom 1,000 to 2,000,000, preferably from 3,000 to 1,500,000, morepreferably from 4,000 to 1,000,000, still preferably from 5,000 to800,000, and even more preferably from 5,000 to 600,000. If the Mn isless than 1,000, physical properties such as mechanical strength andimpact resistance may be insufficient. If the Mn is more than 2,000,000,the melt viscosity may become very high, and then mold processing may bedifficult.

The ratio (Mw/Mn) between the weight average molecular weight (Mw) andnumber average molecular weight (Mn) of the polar group-containingolefin copolymer of the present disclosure, is in a range of generallyfrom 1.0 to 4.0, preferably from 1.3 to 3.5, and more preferably from1.4 to 3.3. If the ratio (Mw/Mn) is less than 1.0, variousprocessability such as molding may be insufficient. If the ratio (Mw/Mn)is more than 4.0, mechanical properties may be inferior.

In the present disclosure, the ratio (Mw/Mn) may be referred to as“molecular weight distribution parameter”.

In the present disclosure, the weight average molecular weight (Mw) andthe number average molecular weight (Mn) are obtained by gel permeationchromatography (GPC).

In the present disclosure, an example of the GPC measurement method isas follows.

The number average molecular weight and the weight average molecularweight can be calculated using high-temperature GPC deviceHLC-8321GPC/HT manufactured by Tosoh Corporation, which is equipped withTSKgel GMHHR-H(S)HT columns manufactured by Tosoh Corporation (two 7.8mm I.D.×30 cm columns in series), by size exclusion chromatography inwhich polystyrene is used as a standard substance for molecular weight(solvent: 1,2-dichlorobenzene, temperature: 145° C.), or the numberaverage molecular weight and the weight average molecular weight can becalculated using high-temperature GPC device ALC/GPC 150C manufacturedby Waters Corporation, which is equipped with AT-806MS columnsmanufactured by Showa Denko K. K. (three 8.0 mm I.D.×25 cm columns inseries), by size exclusion chromatography in which polystyrene is usedas a standard substance for molecular weight (solvent:1,2-dichlorobenzene, temperature: 140° C.).

The melting point (Tm, ° C.) of the polar group-containing olefincopolymer of the present disclosure, which is observed by differentialscanning calorimetry (DSC), is not particularly limited. The meltingpoint is preferably more than 50° C. and 140° C. or less, morepreferably from 60° C. to 138° C., and still more preferably from 70° C.to 135° C. When the melting point is in this range, excellent heatresistance, impact resistance, adhesion, etc. are obtained.

The melting point can be obtained by measurement using, for example,“EXSTAR 6000” manufactured by Seiko Instruments, Inc., when thetemperature is isothermally kept at 40° C. for one minute, increasedfrom 40° C. to 160° C. at 10° C./min, isothermally kept at 160° C. for10 minutes, decreased from 160° C. to 10° C. at 10° C./min, isothermallykept at 10° C. for 5 minutes, and then increased from 10° C. to 160° C.at 10° C./min.

(6) Polar Group-Containing Olefin Copolymer Production Method (6-1)Catalyst

The polar group-containing olefin copolymer of the present disclosuremay be polymerized in the presence of a catalyst containing a transitionmetal, from the viewpoint of ring-opening the one or more monomers (B)selected from the group consisting of polar group-containing monomersrepresented by the general formula (1) and introducing them into themain chain of the polymer in one-step polymerization reaction, and fromthe viewpoint of making the molecular structure of the copolymer alinear molecular structure.

The catalyst containing a transition metal is not particularly limited,as long as it can ring-open the one or more monomers (B) selected fromthe group consisting of polar group-containing monomers represented bythe general formula (1) and can polymerize the ring-opened monomer(s)(B) with the monomer(s) (A). As the catalyst containing a transitionmetal, examples include, but are not limited to, transition metalcompounds of Groups 5 to 11 of the periodic table, which are compoundscontaining a chelating ligand.

Preferred transition metal examples include vanadium, niobium, tantalum,chromium, molybdenum, tungsten, manganese, iron, platinum, ruthenium,cobalt, rhodium, nickel, palladium and copper. Of them, preferred aretransition metals of Groups 8 to 11 of the periodic table; morepreferred are transition metals of Group 10 of the periodic table suchas nickel, palladium and platinum; and particularly preferred are nickel(Ni) and palladium (Pd). These metals may be used solely or incombination of two or more kinds.

The chelating ligand contains at least two atoms selected from the groupconsisting of P, N, O and S. It includes a bidentate or multidentateligand, and it is electrically neutral or anionic. Examples of thestructure are illustrated in reviews by Brookhart, et al. (Chem. Rev.,2000, 100, 1169).

Preferred examples include a bidentate anionic P,O ligand such asphosphorus sulfonate, phosphorus carboxylate, phosphorus phenoxide,phosphorus alkoxide and phosphorus enolate, a bidentate anionic N,Oligand such as salicylaldiminato and pyridine carboxylate. Otherpreferred examples include a diimine ligand, a diphenoxide ligand and adiamide ligand.

From the viewpoint of polymer production efficiency, polymer molecularweight, and copolymerizability of the monomers (A) and (B), the catalystcontaining a transition metal is preferably a catalyst containing a latetransition metal selected from the group consisting of the transitionmetals of Groups 8 to 10 of the periodic table, more preferably acatalyst containing a transition metal of Group 10 of the periodictable, and still more preferably a catalyst containing a transitionmetal of Group 10 of the periodic table, which contains a chelatingligand containing, as a coordination site with the transition metal ofGroup 10 of the periodic table, one or more phosphorus atoms.

From the viewpoint of polymer production efficiency, polymer molecularweight, and copolymerizability of the monomers (A) and (B), the catalystcontaining a transition metal is preferably a catalyst containing atransition metal of Group 10 of the periodic table, which is at leastone selected from the group consisting of compounds represented by thefollowing general formula (104):

where M is a transition metal of Group 10 of the periodic table; Q is adivalent group shown in the brackets of A[—S(═O)₂—O—]M, A[—C(═O)—O—]M,A[—O—]M or A[—S—]M (A and M at the beginning and end of the formulae aredescribed to show the binding direction of the groups); A is a divalenthydrocarbon group containing 1 to 30 carbon atoms, linking Q and thephosphorus atom, and optionally containing a functional group; L is azero-valent ligand capable of leaving from the metal; R¹⁵, R¹⁶ and R¹⁷are each a hydrocarbon group containing 1 to 30 carbon atoms andoptionally containing a functional group; R¹⁵ and L optionally form aring; R¹⁶ and R¹⁷ optionally form a ring; and R¹⁶ or R¹⁷ is optionallybound to A to form a ring.

In the general formula (104), M is a transition metal of Group 10 of theperiodic table, and it is preferably Ni or Pd.

Q is a divalent group represented by —S(═O)₂—O—, —C(═O)—O—, —P(═O)(—OH)—O— or —S—, and it is a moiety where one electron coordinates to M.The left side of each formula is bound to A, and the right side is boundto M. Of them, —S(═O)₂—O— is particularly preferred from the viewpointof catalytic activity.

A is a divalent hydrocarbon group containing 1 to 30 carbon atoms,linking Q and the phosphorus atom, and optionally containing afunctional group.

The divalent hydrocarbon group containing 1 to 30 carbon atoms ispreferably a divalent hydrocarbon group containing 1 to 12 carbon atoms.The divalent hydrocarbon group containing 1 to 30 carbon atoms ispreferably an alkylene group and an arylene group, and particularlypreferably an arylene group.

As the functional group of the hydrocarbon group as A, examples include,but are not limited to, a halogen atom, —OR^(α), —CO₂R^(α), —CO₂M′,—CON(R^(β))₂, —COR^(α), —SR^(α), —SO₂R^(α), —SOR^(α), —OSO₂R^(α),—PO(OR^(α))_(2-y)(R^(β))_(y), —CN, —NHR^(α), —N(R^(α))₂,—Si(OR^(β))_(3-x)(R^(β))_(x), —OSi(OR^(β))_(3-x) (R^(β))_(x), —NO₂,—SO₃M′, —PO₃M′₂, —P(O)(OR^(α))₂M′ and an epoxy-containing group (whereR^(β) is a hydrogen atom or a hydrocarbon group containing 1 to 20carbon atoms; R^(α) is a hydrocarbon group containing 1 to 20 carbonatoms; M′ is an alkali metal, an alkaline-earth metal, an ammonium, aquaternary ammonium or a phosphonium; x is an integer of from 0 to 3;and y is an integer of from 0 to 2).

As the hydrocarbon group containing 1 to 20 carbon atoms, examplesinclude those exemplified above as R^(a) in the general formula (I).

As the divalent hydrocarbon group containing 1 to 30 carbon atoms as A,examples include the following formulae (a-1) to (a-7). In the followingformulae, R¹⁰⁴s are each independently a hydrogen atom, a hydrocarbongroup containing 1 to 30 carbon atoms, or a functional group. As thehydrocarbon group containing 1 to 30 carbon atoms as R¹⁰⁴, examplesinclude those exemplified above as R^(a) in the general formula (I). Thehydrocarbon group containing 1 to 30 carbon atoms is preferably ahydrocarbon group containing 1 to 20 carbon atoms, and more preferably ahydrocarbon group containing 1 to 10 carbon atoms.

From the viewpoint of catalytic activity, the divalent hydrocarbon groupcontaining 1 to 30 carbon atoms as A is preferably the following formula(a-7).

L is a zero-valent ligand capable of leaving from the metal.

L is preferably a compound which contains an electron donating group andwhich can be coordinated with the metal atom M to stabilize the metalcomplex. As L, a hydrocarbon compound containing 1 to 20 carbon atomsand containing oxygen, nitrogen or sulfur as coordinatable atoms, or ahydrocarbon compound containing a carbon-carbon unsaturated bond thatcan be coordinated with the transition metal (and optionally containinga heteroatom) may be used. The number of the carbon atoms of L ispreferably from 1 to 16, and more preferably from 1 to 10.

As L, preferred examples include, but are not limited to, pyridines,piperidines, alkyl ethers, aryl ethers, alkyl aryl ethers, cyclicethers, an alkyl nitrile derivative, an aryl nitrile derivative,alcohols, amides, aliphatic esters, aromatic esters, amines, and cyclicunsaturated hydrocarbons.

As L containing a sulfur atom, examples include dimethyl sulfoxide(DMSO). As L containing a nitrogen atom, examples include, but are notlimited to, trialkylamine containing 1 to 10 carbon atoms in an alkylgroup, dialkylamine containing 1 to carbon atoms in an alkyl group,pyridine, 2,6-dimethylpyridine (also known as 2,6-lutidine), aniline,2,6-dimethylaniline, 2,6-diisopropylaniline,N,N,N′,N′-tetramethylethylenediamine (TMEDA),4-(N,N-dimethylamino)pyridine (DMAP), acetonitrile, benzonitrile,quinoline and 2-methylquinoline. As L containing an oxygen atom,examples include diethyl ether, tetrahydrofuran and 1,2-dimethoxyethane.From the viewpoint of the stability and catalytic activity of thecomplex, dimethyl sulfoxide (DMSO), pyridine, 2,6-dimethylpyridine (alsoknown as 2,6-lutidine) and N,N,N′,N′-tetramethylethylenediamine (TMEDA)are preferred, and dimethyl sulfoxide (DMSO) and 2,6-dimethylpyridine(also known as 2,6-lutidine) are more preferred.

R¹⁵ and L may form a ring. An example thereof is a cycloocta-1-enylgroup, which is also a preferred embodiment in the present disclosure.

R¹⁵, R¹⁶ and R¹⁷ are each a hydrocarbon group containing 1 to 30 carbonatoms and optionally containing a functional group. As the hydrocarbongroup containing 1 to 30 carbon atoms as R¹⁵, R¹⁶ and R¹⁷, examplesinclude those exemplified above as R^(a) in the general formula (I).

The functional group in R¹⁵, R¹⁶ and R¹⁷ may be the same as thefunctional group in A.

R¹⁵ is preferably a hydrocarbon group containing 1 to 20 carbon atoms, ahalogen-substituted hydrocarbon group containing 1 to 20 carbon atoms,or a hydrocarbon group containing 1 to 20 carbon atoms and beingsubstituted with an alkoxy group or an aryloxy group. The number of thecarbon atoms of the hydrocarbon group is more preferably from 1 to 10.In particular, R¹⁵ is more preferably an alkyl group containing 1 to 3carbon atoms, a benzyl group, a trifluoromethyl group, apentafluorophenyl group, a 1-(methoxymethyl)ethyl group, a1-(ethoxymethyl)ethyl group, a 1-(phenoxymethyl)ethyl group, or a1-(2,6-dimethylphenoxymethyl)ethyl group, and R¹⁵ is still morepreferably a methyl group or a benzyl group.

R¹⁶ and R¹⁷ are located in the neighborhood of the transition metal M,and they sterically and/or electronically exert an interaction on thetransition metal M. To exert such an effect, R¹⁶ and R¹⁷ are preferablybulky. The number of the carbon atoms of R¹⁶ and R¹⁷ is preferably from3 to 30, and more preferably from 6 to 20.

R¹⁶ and R¹⁷ are each preferably an alkyl group containing 3 to 10 carbonatoms and optionally containing a functional group, a cycloalkyl groupcontaining 6 to 20 carbon atoms and optionally containing a functionalgroup, or an aryl group containing 6 to 20 carbon atoms and optionallycontaining a functional group.

The alkyl group containing 3 to 10 carbon atoms as R¹⁶ and R¹⁷ ispreferably an n-propyl group, an isopropyl group, an n-butyl group, anisobutyl group, a sec-butyl group or a t-butyl group.

As the cycloalkyl group containing 6 to 20 carbon atoms and optionallycontaining a functional group as R¹⁶ and R¹⁷, examples include, but arenot limited to, a cyclohexyl group, a cycloheptyl group and a cyclooctylgroup, all of which optionally contain a functional group and optionallyare substituted with a linear or branched alkyl group containing 3 to 10carbon atoms.

The cycloalkyl group may be the cycloalkyl group described in paragraphs0104 to 0113 in JP-A No. 2018-141138 (X in the paragraphs 0104 to 0113in JP-A No. 2018-141138 indicates the binding site of P (a phosphorusatom) in the general formula (104) of the present disclosure).

From the viewpoint of polymer molecular weight control and polar monomercopolymerizability control, R¹⁶ and R¹⁷ are preferably a cyclohexylgroup optionally being substituted with a linear or branched alkyl groupcontaining 3 to 10 carbon atoms, and more preferably a cyclohexyl groupbeing substituted with a linear or branched alkyl group containing 3 to10 carbon atoms. R¹⁶ and R¹⁷ are more preferably a2-isopropyl-5-methylcyclohexyl group (a menthyl group).

As the aryl group containing 6 to 20 carbon atoms and optionallycontaining a functional group as R¹⁶ and R¹⁷, examples include, but arenot limited to, a phenyl group, a naphthyl group and an anthracenylgroup, all of which optionally contain a functional group and optionallyare substituted with a linear or branched alkyl group containing 3 to 10carbon atoms. The aryl group containing 6 to 20 carbon atoms ispreferably substituted with a group containing at least one of an oxygenatom and a nitrogen atom. When the aryl group containing 6 to 20 carbonatoms is substituted with a group containing at least one of an oxygenatom and a nitrogen atom, the functional group is preferably substitutedat the ortho position with respect to carbon bound to phosphorus,because, as a result, at least one of the oxygen atom and nitrogen atomin R¹⁶ and R¹⁷ can be spatially arranged so as to possess an interactionwith the transition metal M.

As R¹⁶ and R¹⁷, preferred examples include, but are not limited to, a2,6-dimethoxyphenyl group, a 2,4,6-trimethoxyphenyl group, a4-methyl-2,6-dimethoxyphenyl group, a 4-t-butyl-2,6-dimethoxyphenylgroup, a 1,3-dimethoxy-2-naphthyl group, a 2,6-diethoxyphenyl group, a2,4,6-triethoxyphenyl group, a 4-methyl-2,6-diethoxyphenyl group, a4-t-butyl-2,6-diethoxyphenyl group, a 1,3-diethoxy-2-naphthyl group, a2,6-diphenoxyphenyl group, a 2,4,6-triphenoxyphenyl group, a4-methyl-2,6-diphenoxyphenyl group, a 4-t-butyl-2,6-diphenoxyphenylgroup, a 1,3-diphenoxy-2-naphthyl group, a 2,6-dimethoxymethylphenylgroup, a 2,4,6-trimethoxymethylphenyl group, a4-methyl-2,6-dimethoxymethylphenyl group, a4-t-butyl-2,6-dimethoxymethylphenyl group, a1,3-dimethoxymethyl-2-naphthyl group, a 2,6-diphenoxymethylphenyl group,a 2,4,6-triphenoxymethylphenyl group, a4-methyl-2,6-diphenoxymethylphenyl group, a4-t-butyl-2,6-diphenoxymethylphenyl group, a1,3-diphenoxymethyl-2-naphthyl group, a 2,6-di(2-methoxyethyl)phenylgroup, a 2,4,6-tri(2-methoxyethyl)phenyl group, a 4-methyl-2,6-di(2-methoxyethyl)phenyl group, a 4-t-butyl-2,6-di (2-methoxyethyl)phenylgroup, a 1,3-di (2-methoxyethyl)-2-naphthyl group, a2,6-di(2-phenoxyethyl)phenyl group, a 2,4,6-tri(2-phenoxyethyl)phenylgroup, a 4-methyl-2,6-di (2-phenoxyethyl)phenyl group, a4-t-butyl-2,6-di(2-phenoxyethyl)phenyl group, and a1,3-di(2-phenoxyethyl)-2-naphthyl group.

R¹⁶ or R¹⁷ may be bound to A to form a ring structure. As the ringstructure, examples include the structures described in paragraphs 0120and 0121 in JP-A No. 2018-141138 (these examples indicate the case wherethe substituent R¹⁶ and A are bound to form a ring structure, and P andQ are the same as those shown in the general formula (104) of thepresent disclosure).

Among the compounds represented by the general formula (104) of thepresent disclosure, the compound represented by the following generalformula (105) is preferred from the viewpoint of polymer productionefficiency:

where M, L, R¹⁵, R¹⁶ and R¹⁷ are the same as those of the generalformula (104), and R¹¹¹, R¹¹², R¹¹³ and R¹¹⁴ are each independently ahydrogen atom, a hydrocarbon group containing 1 to 30 carbon atoms or afunctional group.

In the general formula (105), the hydrocarbon group containing 1 to 30carbon atoms and the functional group as R¹¹¹, R¹¹², R¹¹³ and R¹¹⁴ maybe the same as those described above for A.

Of them, R¹¹¹ tends to give a high-molecular-weight polymer when it isbulky, and a functional group such as a t-butyl group, a trimethylsilylgroup, a phenyl group, a 9-anthracenyl group, a 4-t-butylphenyl group, a2,4-di-t-butylphenyl group and a pentafluorophenyl group may beappropriately selected.

The transition metal complex used in the present disclosure can beprepared by a conventionally known method.

The catalyst containing a transition metal used in the presentdisclosure, is a catalyst which contains, as a main catalyst component,the above-described transition metal complex. As needed, it may be usedin combination with an activator, a carrier, etc. As the activator,examples include alkylalumoxane, which is a promoter used in metallocenecatalyst, and a boron-containing compound.

As the carrier, any carrier can be used as long as it does not departfrom the gist of the present invention. In general, an inorganic oxideor a polymer carrier is preferably used.

As the carrier, examples include, but are not limited to, SiO₂, Al₂O₃,MgO, ZrO₂, TiO₂, B203, CaO, ZnO, BaO, ThO₂, and mixtures thereof. Also,a mixed oxide such as SiO₂—Al₂O₃, SiO₂—V₂O₅, SiO₂—TiO₂, SiO₂—MgO andSiO₂—Cr₂O₃ can be used. Also, inorganic silicate, a polyethylenecarrier, a polypropylene carrier, a polystyrene carrier, a polyacrylicacid carrier, a polymethacrylic acid carrier, a polyacrylic acid estercarrier, a polyester carrier, a polyamide carrier, a polyimide carrierand the like can be used. For these carriers, the particle diameter,particle size distribution, pore volume, specific surface area and so onare not particularly limited, and any carrier can be used.

(6-2) Polar Group-Containing Olefin Copolymer Polymerization Method

In the present disclosure, the method for polymerizing the polargroup-containing olefin copolymer is not particularly limited.

For example, solution polymerization in which all of the producedpolymer is dissolved in a medium, slurry polymerization in which atleast a part of the produced polymer is made into slurry in a medium,bulk polymerization in which a liquefied monomer itself is used as amedium, or high-pressure ion polymerization in which at least a part ofthe produced polymer is dissolved in a monomer liquefied at hightemperature and high pressure, may be used.

The polymerizing method may be any of batch polymerization, semi-batchpolymerization and continuous polymerization.

Detailed production processes and conditions are disclosed in JP-A Nos.2010-260913 and 2010-202647, for example.

An unreacted monomer and the medium may be separated from the producedpolymer, recycled and used. In the recycling process, the monomer andthe medium may be purified and reused, or they may be reused withoutpurification. Conventionally-known methods may be used for separation ofthe unreacted monomer and the medium from the produced polymer, such asfiltration, centrifugal separation, solvent extraction, andreprecipitation using a poor solvent.

The copolymerization temperature, copolymerization pressure andcopolymerization time are not particularly limited. In general, they maybe appropriately set in the following ranges, considering productivityand process capability.

The copolymerization temperature is in a range of generally from −20° C.to 290° C., preferably from 0° C. to 250° C., more preferably from 0° C.to 200° C., still more preferably from 10° C. to 150° C., andparticularly preferably from 20° C. to 100° C. The copolymerizationpressure is in a range of generally from 0.1 MPa to 100 MPa, preferablyfrom 0.3 MPa to 90 MPa, more preferably from 0.5 MPa to 80 MPa, stillmore preferably from 1.0 MPa to 70 MPa, and particularly preferably from1.3 MPa to 60 MPa. The copolymerization time is in a range of generallyfrom 0.1 minute to 50 hours, preferably from 0.5 minute to 40 hours, andmore preferably from one minute to 30 hours.

In the present invention, the polymerization is generally carried out inan inert gas atmosphere. For example, a nitrogen or argon atmosphere isused, and a nitrogen atmosphere is preferably used.

The supply of the catalyst and monomers to a polymerization reactor isnot particularly limited. Various supplying methods are availabledepending on the purpose. For example, in the case of batchpolymerization, the following method can be employed: the monomers inpredetermined amounts are supplied to a copolymerization reactor inadvance, and then the catalyst is supplied thereto. In this case, anadditional monomer and an additional catalyst may be supplied to thecopolymerization reactor. In the case of continuous polymerization, thefollowing method can be employed: the monomers and catalyst inpredetermined amounts are continuously or intermittently supplied to acopolymerization reactor to continuously carry out a copolymerizationreaction.

For controlling the composition of the copolymer, a method forcontrolling the composition by changing the ratio of the suppliedmonomers, can be generally employed. Also, a method for controlling thecopolymer composition by utilizing a difference in monomer reactivityratio, which is due to a difference in catalyst structure, may beemployed, or a method for controlling the copolymer composition byutilizing the polymerization temperature dependence of the monomerreactivity ratio, may be employed.

For the control of the molecular weight of the copolymer, aconventionally-known method can be employed, such as a method forcontrolling the molecular weight by controlling the polymerizationtemperature, a method for controlling the molecular weight bycontrolling the monomer concentration, and a method for controlling themolecular weight by controlling the ligand structure in the transitionmetal complex.

EXAMPLES

Hereinafter, the present disclosure will be described in more detail,with reference to examples and comparative examples. The presentdisclosure is not limited to these examples, as long as it does notdepart from the gist of the present invention. The physical propertiesand so on of the polar group-containing olefin copolymer and so on weremeasured by the following method.

[Structure of the Polar Group-Containing Olefin Copolymer]

The structure of the polar group-containing olefin copolymer wasdetermined by ¹H-NMR and ¹³C-NMR analysis using ASCEND 500 manufacturedby BRUKER or AVANCE 400 manufactured by BRUKER.

The NMR measurement was carried out at 120° C. in the followingconditions: 1,1,2,2-tetrachloroethane-d2 was used as the solvent; thepolymer concentration for the ¹H-NMR measurement was 5 mass %; and thepolymer concentration for the ¹³C-NMR measurement was 15 mass %. Or, apart of the NMR measurement was carried out at 120° C. with a uniformsolution in which about 150 mg of the polar group-containing olefincopolymer was dissolved by heating in 2.4 mL of a mixed solvent(1,2-dichlorobenzene:bromobenzene-d5=1:2).

The ¹³C-NMR was measured using chromium(III) acetylacetonate as arelaxation reagent and using an inverse-gated decoupling method (a 90°pulse of 9.0 microseconds, spectral width: 31 kHz, relaxation time: 10seconds, acquisition time: 10 seconds, and accumulated number of timesof FID: 5,000 to 10,000), and then quantitative analysis was performed.Or, a part of the ¹³C-NMR was measured using an inverse-gated decouplingmethod (a 90° pulse of 15.8 microseconds, spectral width: 25 kHz,relaxation time: 50 seconds, acquisition time: 1.5 seconds, andaccumulated number of times of FID: 1,024), and then quantitativeanalysis was performed.

[Number Average Molecular Weight and Weight Average Molecular Weight]

The number average molecular weight and the weight average molecularweight were calculated using high-temperature GPC device HLC-8321GPC/HTmanufactured by Tosoh Corporation, which was equipped with TSKgelGMHHR-H(S)HT columns manufactured by Tosoh Corporation (two 7.8 mmI.D.×30 cm columns in series), by size exclusion chromatography in whichpolystyrene was used as a standard substance for molecular weight(solvent: 1,2-dichlorobenzene, temperature: 145° C.), or the numberaverage molecular weight and the weight average molecular weight werecalculated using high-temperature GPC device ALC/GPC 150C manufacturedby Waters Corporation, which was equipped with AT-806MS columnsmanufactured by Showa Denko K. K. (three 8.0 mm I.D.×25 cm columns inseries), by size exclusion chromatography in which polystyrene was usedas a standard substance for molecular weight (solvent:1,2-dichlorobenzene, temperature: 140° C.).

Synthesis of the Transition Metal Complex Synthesis Example 1

A transition metal complex (A) represented by the following chemicalformula (A) (where both Rs are menthyl(2-isopropyl-5-methylcyclohexyl)and Lut is 2,6-dimethylpyridine) was synthesized as described in JP-ANo. 2017-031300.

Synthesis Example 2

A transition metal complex (B) represented by the chemical formula (A)(where both Rs are cyclohexyl and Lut is 2,6-dimethylpyridine) wassynthesized as described in JP-A No. 2011-068881.

Synthesis Example 3

A transition metal complex (C) represented by the chemical formula (A)(where both Rs are isopropyl and Lut is 2,6-dimethylpyridine) wassynthesized as described in JP-A No. 2013-079347.

Synthesis Example 4

A transition metal complex (D) represented by the chemical formula (A)(where both Rs are 2-methoxyphenyl and Lut is 2,6-dimethylpyridine) wassynthesized as described in JP-A No. 2007-046032.

Example 1

In a nitrogen atmosphere, the transition metal complex (A) (6.9 mg,0.010 mmol) as the catalyst, toluene (10 mL) as the solvent, and2,3-diphenylcyclopropen-1-one (206.1 mg, 1.0 mmol) as the monomer (B)were added in a 50 mL autoclave in sequence. While the autoclave waspressurized with ethylene (the monomer (A)) (3.0 MPa), the mixture wasstirred at a reaction temperature of 80° C. for 12 hours. The autoclavewas returned to room temperature, and methanol (20 mL) was added. Asolid thus precipitated was recovered by filtration, washed withmethanol, and then dried under reduced pressure. A polargroup-containing olefin polymer 1 thus obtained was 2035 mg.

The polymerization conditions are shown in Table 1, and the results ofvarious analyses of the polar group-containing olefin polymer 1 areshown in Table 2. FIG. 1 shows the ¹H-NMR spectrum of the obtainedpolymer 1. FIG. 2 is a partially enlarged view (8.00 ppm to 0 ppm) ofthe ¹H-NMR spectrum of the polymer 1. FIG. 3 shows the 13C-NMR spectrumof the polymer 1. FIG. 4 shows the GPC chart of the polymer 1. FIG. 5shows the DSC chart of the polymer 1.

Example 2

Example 2 was carried out in the same manner as Example 1, except thatthe catalyst was changed to the transition metal complex (B) (5.8 mg,0.010 mmol). A polar group-containing olefin polymer 2 thus obtained was976 mg.

The results of various analyses of the polar group-containing olefinpolymer 2 are shown in Table 2. FIG. 1 shows the ¹H-NMR spectrum of theobtained polymer 2.

Example 3

Example 3 was carried out in the same manner as Example 1, except thatthe catalyst was changed to the transition metal complex (C) (5.0 mg,0.010 mmol). A polar group-containing olefin polymer 3 thus obtained was1420 mg.

The results of various analyses of the polar group-containing olefinpolymer 3 are shown in Table 2. FIG. 1 shows the ¹H-NMR spectrum of theobtained polymer 3.

Example 4

Example 4 was carried out in the same manner as Example 1, except thatthe catalyst was changed to the transition metal complex (D) (6.3 mg,0.010 mmol). A polar group-containing olefin polymer 4 thus obtained was526 mg.

The results of various analyses of the polar group-containing olefinpolymer 4 are shown in Table 2. FIG. 1 shows the ¹H-NMR spectrum of theobtained polymer 4.

Example 5

Example 5 was carried out in the same manner as Example 1, except thatthe reaction temperature was changed to 60° C. A polar group-containingolefin polymer 5 thus obtained was 896 mg.

The results of various analyses of the polar group-containing olefinpolymer 5 are shown in Table 2.

Example 6

Example 6 was carried out in the same manner as Example 1, except thatthe reaction temperature was changed to 120° C. A polar group-containingolefin polymer 6 thus obtained was 1446 mg.

The results of various analyses of the polar group-containing olefinpolymer 6 are shown in Table 2.

Example 7

Example 7 was carried out in the same manner as Example 1, except thatthe ethylene pressure was changed to 1 MPa. A polar group-containingolefin polymer 7 thus obtained was 275 mg.

The results of various analyses of the polar group-containing olefinpolymer 7 are shown in Table 2.

Example 8

Example 8 was carried out in the same manner as Example 1, except thatthe monomer (B) was changed to 2,3-diphenylcyclopropen-1-one (1030.5 mg,5.0 mmol). A polar group-containing olefin polymer 8 thus obtained was408 mg.

The results of various analyses of the polar group-containing olefinpolymer 8 are shown in Table 2.

Example 9

Example 9 was carried out in the same manner as Example 1, except thatthe monomer (B) was changed to 2,3-di(4-methoxyphenyl)cyclopropen-1-one(266.3 mg, 1.0 mmol). A polar group-containing olefin polymer 9 thusobtained was 436 mg. The results of various analyses of the polargroup-containing olefin polymer 9 are shown in Table 2. FIG. 6 shows the¹H-NMR spectrum of the obtained polymer 9.

Example 10

Example 10 was carried out in the same manner as Example 1, except thatthe monomer (B) was changed to 2,3-di(4-bromophenyl)cyclopropen-1-one(364.0 mg, 1.0 mmol). A polar group-containing olefin polymer 10 thusobtained was 1467 mg. The results of various analyses of the polargroup-containing olefin polymer 10 are shown in Table 2. FIG. 7 showsthe ¹H-NMR spectrum of the obtained polymer 10.

Example 11

Example 11 was carried out in the same manner as Example 1, except thatthe monomer (B) was changed to 2,3-diethylcyclopropen-1-one (110.1 mg,1.0 mmol). A polar group-containing olefin polymer 11 thus obtained was479 mg.

The results of various analyses of the polar group-containing olefinpolymer 11 are shown in Table 2. FIG. 8 shows the ¹H-NMR spectrum of theobtained polymer 11.

Example 12

Example 12 was carried out in the same manner as Example 1, except thatallyl acetate (1852.2 mg, 18.5 mmol) was further added as the monomer(C). A polar group-containing olefin polymer 12 thus obtained was 206mg.

The results of various analyses of the polar group-containing olefinpolymer 12 are shown in Table 2. FIG. 9 shows the ¹H-NMR spectrum of theobtained polymer 12.

Example 13

In a nitrogen atmosphere, toluene (400 mL) as the solvent and3-ethyl-2-phenylcyclopropen-1-one (3.12 g, 20 mmol) as the monomer (B)were added in a 2.4 L autoclave in sequence. The autoclave waspressurized with ethylene (the monomer (A)) (3.0 MPa); the transitionmetal complex (A) (278 mg, 0.40 mmol) as the catalyst was added; and themixture was stirred at a reaction temperature of 80° C. for 1 hour. Atoluene solution of 1,2-butanediol (1 M, 10 mL) was added; the autoclavewas returned to room temperature; and EKINEN (trade name) F-1(manufactured by Japan Alcohol Trading Co., Ltd., 500 mL) was added. Asolid thus precipitated was recovered by filtration, washed with EKINEN(trade name) F-1 (500 mL×2), and then dried under reduced pressure. Apolar group-containing olefin polymer 13 thus obtained was 3720 mg.

The results of various analyses of the polar group-containing olefinpolymer 13 are shown in Table 2. FIG. 10 shows the ¹³C-NMR spectrum ofthe obtained polymer 13.

Example 14

In a nitrogen atmosphere, toluene (400 mL) as the solvent and2-diethylamino-3-(4-methoxyphenyl)cyclopropen-1-one (578 mg, 2.5 mmol,containing about 10 mol % of2-diethylamino-3-(2-methoxyphenyl)cyclopropen-1-one as impurity) as themonomer (B) were added in a 2.4 L autoclave in sequence. The autoclavewas pressurized with ethylene (the monomer (A)) (3.0 MPa) and at areaction temperature of 80° C., the transition metal complex (A) (278mg, 0.40 mmol) as the catalyst was added. After the elapse of 10 minutesfrom the start of the reaction,2-diethylamino-3-(4-methoxyphenyl)cyclopropen-1-one (578 mg, 2.5 mmol)was further added. After the elapse of 1 hour from the addition of thecatalyst, a toluene solution of 1,2-butanediol (1 M, 10 mL) was added;the autoclave was returned to room temperature; and EKINEN (trade name)F-1 (500 mL) was added. A solid thus precipitated was recovered byfiltration, washed with EKINEN (trade name) F-1 (500 mL×2), and thendried under reduced pressure. A polar group-containing olefin polymer 14thus obtained was 9640 mg.

The results of various analyses of the polar group-containing olefinpolymer 14 are shown in Table 2. FIG. 11 shows the 13C-NMR spectrum ofthe obtained polymer 14.

Example 15

In a nitrogen atmosphere, toluene (410 mL) as the solvent and2-ethoxy-3-phenylcyclopropen-1-one (653 mg, 3.75 mmol) as the monomer(B) were added in a 2.4 L autoclave in sequence. The autoclave waspressurized with ethylene (the monomer (A)) (3.0 MPa) and at a reactiontemperature of 80° C., the transition metal complex (A) (278 mg, 0.40mmol) as the catalyst was added. After the elapse of 1 hour from theaddition of the catalyst, a toluene solution of 1,2-butanediol (1 M, 10mL) was added; the autoclave was returned to room temperature; andacetone (500 mL) was added. A solid thus precipitated was recovered byfiltration, washed with acetone (500 mL×2), and then dried under reducedpressure. A polar group-containing olefin polymer 15 thus obtained was5160 mg.

The results of various analyses of the polar group-containing olefinpolymer 15 are shown in Table 2. FIGS. 12 and 13 show the ¹H-NMRspectrum and ¹³C-NMR spectrum of the polymer 15, respectively. Thepolymer 15 failed in peak separation in ¹H-NMR and failed to quantitatethe structure of β. Accordingly, “n.d.” (not determined) is mentioned inTable 2.

TABLE 1 Catalyst Catalyst amount Temperature Time Monomer (A) Monomer(B) Monomer (C) Example type [mmol] [° C.] [h] Type MPa Type [mmol] Type[mmol]  1 A 0.01 80 12 Ethylene 3 2,3-Diphenylcyclopropen-1-one 1 — —  2B 0.01 80 12 Ethylene 3 2,3-Diphenylcyclopropen-1-one 1 — —  3 C 0.01 8012 Ethylene 3 2,3-Diphenylcyclopropen-1-one 1 — —  4 D 0.01 80 12Ethylene 3 2,3-Diphenylcyclopropen-1-one 1 — —  5 A 0.01 60 12 Ethylene3 2,3-Diphenylcyclopropen-1-one 1 — —  6 A 0.01 120 12 Ethylene 32,3-Diphenylcyclopropen-1-one 1 — —  7 A 0.01 80 12 Ethylene 12,3-Diphenylcyclopropen-1-one 1 — —  8 A 0.01 80 12 Ethylene 32,3-Diphenylcyclopropen-1-one 5 — —  9 A 0.01 80 12 Ethylene 32,3-Di(4-methoxyphenyl)cyclo- 1 — — propen-1-one 10 A 0.01 80 12Ethylene 3 2,3-Di(4-bromophenyl)cyclo- 1 — — propen-1-one 11 A 0.01 8012 Ethylene 3 2,3-Diethylcyclopropen-1-one 1 — — 12 A 0.01 80 12Ethylene 3 2,3-Diphenylcyclopropen-1-one 1 Allyl 18.5 acetate 13 A 0.4080  1 Ethylene 3 3-Ethyl-2-phenylcyclopropen-1-one 20 — — 14 A 0.40 80 1 Ethylene 3 2-Diethylamino-3- 5 — — (4-methoxyphenyl)cyclopropen-1-one15 A 0.40 80  1 Ethylene 3 2-Ethoxy-3-phenylcyclopropen-1-one 3.75 — —

TABLE 2 Structural Structural Structural Catalytic unit (B) Structureunit unit Yield activity Mn Mw/ (Structure of α) of β (A) (C) ExamplePolymer (g) (kg/mol/h) (g/mol) Mn (mol %) (mol %) (mol %) (mol %)  1 12.035 17.0 25,300 2.5 1.01 0.17 98.82 —  2 2 0.976 8.1 7,600 2.3 0.840.35 98.81 —  3 3 1.420 11.8 7,600 2.1 0.68 0.20 99.12 —  4 4 0.526 4.45,400 2.6 1.86 1.00 97.14 —  5 5 0.896 7.5 50,600 1.8 0.41 0.04 99.55 — 6 6 1.446 12.1 13,800 2.4 0.83 0.91 98.26 —  7 7 0.275 2.3 5,500 1.63.18 1.32 95.50 —  8 8 0.408 3.4 5,400 1.4 3.93 1.79 94.28 —  9 9 0.4363.6 4,000 2.4 0.88^(※) 99.12 — 10 10 1.467 12.2 11,200 2.4 0.34 0.0199.65 — 11 11 0.479 4.0 5,200 3.3 0.39 <0.01 99.61 — 12 12 0.206 1.76,900 2.2 1.27 0.20 97.91 0.62 13 13 3.72 9.3 5,900 1.9 1.55 0.54 97.91— 14 14 9.64 24.1 10,700 2.3 0.03 0.03 99.94 — 15 15 5.16 12.9 16,2002.0 0.02 n.d. 99.98 — ^(※)Total of α and β structures of Polymer 9 n.d.= not determined

As is clear from the NMR measurement results, the novel polargroup-containing olefin copolymer in which, as the structural unit (B),an enone structure is introduced into the main chain, was obtained.

In Table 2, the structure of a (mol %) means the percentage of thecontained structural unit (B) represented by the general formula (I)when the whole structural units of the polymer are defined as 100 mol %.The structure of a (mol %) means the percentage of the containedstructural unit represented by the formula (II) when the wholestructural units of the polymer are defined as 100 mol %.

INDUSTRIAL APPLICABILITY

In the novel polar group-containing olefin polymer of the presentdisclosure, as a structural unit, an enone structure is introduced intothe main chain. Accordingly, the novel polar group-containing olefinpolymer of the present disclosure can be used as a substrate foraddition reaction, condensation reaction, etc., or as a polymerizablemonomer, and it is expected to be a raw material that can be transformedinto various composite materials. When the enone structure of the polargroup-containing olefin polymer of the present disclosure contains afunctional group, the functional group in the enone structure mayfunction as a leaving group and may become the starting point forintroducing a different substituent, and the enone structure may havechelate coordination properties with metals. Due to this function, thenovel polar group-containing olefin polymer of the present disclosure isalso expected to be usable as a carrier for metal complex catalysts, anabsorbent for metal complex recovery, etc. Also, depending on the typeof the functional group introduced into the enone structure, the novelpolar group-containing olefin polymer of the present disclosure isapplicable to pigments, dyes, medicines, etc.

1. A polar group-containing olefin copolymer comprising a structuralunit (A) derived from one or more monomers selected from the groupconsisting of ethylene and an olefin containing 3 to 20 carbon atoms,and a structural unit (B) represented by the following general formula(I):

where R^(x) and R^(y) are each independently a hydrogen atom, a halogenatom, a hydroxyl group, a formyl group, an ester group containing 1 to30 carbon atoms, an acyloxy group containing 1 to 30 carbon atoms, anacyl group containing 1 to 30 carbon atoms, an alkoxy group containing 1to 30 carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, analkylthio group containing 1 to 30 carbon atoms, an arylthio groupcontaining 6 to 30 carbon atoms, a nitro group, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or R^(x) and R^(y) are optionally bound to each other toform a 4- to 10-membered ring.
 2. The polar group-containing olefincopolymer according to claim 1, wherein the structural unit (B)represented by the general formula (I) is derived from one or moremonomers selected from the group consisting of polar group-containingmonomers represented by the following general formula (1):

where R^(x) and R^(y) are each independently a hydrogen atom, a halogenatom, a hydroxyl group, a formyl group, an ester group containing 1 to30 carbon atoms, an acyloxy group containing 1 to 30 carbon atoms, anacyl group containing 1 to 30 carbon atoms, an alkoxy group containing 1to 30 carbon atoms, an aryloxy group containing 6 to 30 carbon atoms, analkylthio group containing 1 to 30 carbon atoms, an arylthio groupcontaining 6 to 30 carbon atoms, a nitro group, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or R^(x) and R^(y) are optionally bound to each other toform a 4- to 10-membered ring.
 3. The polar group-containing olefincopolymer according to claim 1, wherein at least one of R^(x) and R^(y)is different from a hydrogen atom.
 4. The polar group-containing olefincopolymer according to claim 1, further comprising a structural unit (C)derived from one or more monomers selected from the group consisting ofa polar group-containing monomer (c-1) represented by the followinggeneral formula (2) and a polar group-containing monomer (c-2)represented by the following general formula (3):

where R¹ and R² are each independently a hydrogen atom, an ester groupcontaining 1 to 30 carbon atoms, an acyloxy group containing 1 to 30carbon atoms, an alkoxy group containing 1 to 30 carbon atoms, anaryloxy group containing 6 to 30 carbon atoms, a cyano group, an aminogroup optionally being substituted with a hydrocarbon group containing 1to 30 carbon atoms, an amide group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, an imino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, or a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atom,a nitrogen atom and a phosphorus atom, and at least one of R¹ and R² isa group containing at least one of an oxygen atom and a nitrogen atom,and

where R³ to R¹⁰ are each independently a hydrogen atom, a halogen atomor a hydrocarbon group containing 1 to 20 carbon atoms; n is 0 or apositive integer, and when n is 2 or more, R⁷ to R¹⁰ are each optionallythe same or different in each repeating unit; R¹¹ to R¹⁴ are eachindependently a hydrogen atom, an ester group containing 1 to 30 carbonatoms, an acyloxy group containing 1 to 30 carbon atoms, an alkoxy groupcontaining 1 to 30 carbon atoms, an aryloxy group containing 6 to 30carbon atoms, a cyano group, an amino group optionally being substitutedwith a hydrocarbon group containing 1 to 30 carbon atoms, an amide groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, an imino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, or a hydrocarbongroup containing 1 to 30 carbon atoms and optionally being substitutedwith a functional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom, a nitrogen atom and aphosphorus atom, and at least one of R¹¹ to R¹⁴ is a group containing atleast one of an oxygen atom and a nitrogen atom; and R¹¹ and R¹² areoptionally integrated to form a divalent organic group, and R¹³ and R¹⁴are optionally integrated to form a divalent organic group; R¹¹ or R¹²optionally forms a ring with R¹³ or R¹⁴.
 5. The polar group-containingolefin copolymer according to claim 1, wherein the structural unit (A)is a structural unit derived from ethylene.
 6. The polargroup-containing olefin copolymer according to claim 1, wherein R^(x)and R^(y) are each independently a hydrogen atom, a hydroxyl group, aformyl group, an ester group containing 1 to 30 carbon atoms, an acylgroup containing 1 to 30 carbon atoms, an alkoxy group containing 1 to30 carbon atoms, an amino group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, a silyl groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a halogen-substituted hydrocarbon group containing 1 to 30carbon atoms, a hydrocarbon group containing 1 to 30 carbon atoms andoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or a heterocyclic group optionally beingsubstituted with a functional group containing at least one selectedfrom the group consisting of an oxygen atom, a sulfur atom and anitrogen atom, or R^(x) and R^(y) are optionally bound to each other toform a 4- to 10-membered ring, and wherein at least one of R^(x) andR^(y) is different from a hydrogen atom.
 7. The polar group-containingolefin copolymer according to claim 1, wherein R^(x) and R^(y) are eachindependently a halogen atom, a hydroxyl group, a formyl group, an estergroup containing 1 to 30 carbon atoms, an acyloxy group containing 1 to30 carbon atoms, an acyl group containing 1 to 30 carbon atoms, analkoxy group containing 1 to 30 carbon atoms, an aryloxy groupcontaining 6 to 30 carbon atoms, an alkylthio group containing 1 to 30carbon atoms, an arylthio group containing 6 to 30 carbon atoms, anamino group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, a silyl group optionally beingsubstituted with a hydrocarbon group containing 1 to 30 carbon atoms, anamide group optionally being substituted with a hydrocarbon groupcontaining 1 to 30 carbon atoms, a halogen-substituted hydrocarbon groupcontaining 1 to 30 carbon atoms, a hydrocarbon group containing 1 to 30carbon atoms and optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom, or a heterocyclic groupoptionally being substituted with a functional group containing at leastone selected from the group consisting of an oxygen atom, a sulfur atomand a nitrogen atom, or R^(x) and R^(y) are optionally bound to eachother to form a 4- to 10-membered ring.
 8. The polar group-containingolefin copolymer according to claim 1, wherein R^(x) and R^(y) are eachindependently a hydroxyl group, a formyl group, an ester groupcontaining 1 to 30 carbon atoms, an acyl group containing 1 to 30 carbonatoms, an alkoxy group containing 1 to 30 carbon atoms, an amino groupoptionally being substituted with a hydrocarbon group containing 1 to 30carbon atoms, a silyl group optionally being substituted with ahydrocarbon group containing 1 to 30 carbon atoms, a halogen-substitutedhydrocarbon group containing 1 to 30 carbon atoms, a hydrocarbon groupcontaining 1 to 30 carbon atoms and optionally being substituted with afunctional group containing at least one selected from the groupconsisting of an oxygen atom, a sulfur atom and a nitrogen atom, or aheterocyclic group optionally being substituted with a functional groupcontaining at least one selected from the group consisting of an oxygenatom, a sulfur atom and a nitrogen atom, or R^(x) and R^(y) areoptionally bound to each other to form a 4- to 10-membered ring.